| Identification | Back Directory | [Name]
N,N'-BIS-TERT-BUTOXYCARBONYLTHIOUREA | [CAS]
145013-05-4 | [Synonyms]
Diboc-thiourea
BIS-BOC-THIOUREA
1,3-Di-Boc-thiourea
N,Nμ-Di-Boc-thiourea
N,N`-Di-Boc-thiourea,97%
N,N'-Di-Boc-thiourea 97%
Bis-Boc-thiourea Novabiochem
-BIS-TERT-BUTOXYCARBONYLTHIOUREA
1,3-Bis(tert-butoxycarbonyl)thiourea
N,N'DI-(TERT-BUTOXYCARBONYL)THIOUREA
N,N'-BIS-TERT-BUTOXYCARBONYLTHIOUREA
N,N'-BIS-TERT-BUTOXYCARBONYLTHIOUREA
1,3-Bis(tert-butoxycarbonyl)thiourea >
N,N'-bis(1,1-diMethylethoxycarbonyl)thiourea
N,N′-Bis-tert-butoxycarbonylthiourea USP/EP/BP
N,N'-Di-(tert-Butoxycarbonyl)thiourea≥ 98% (HPLC)
ert-butylN-[(2-methylpropan-2-yl)oxycarbonylcarbamothioyl]carbamate
tert-butyl N-[(2-methylpropan-2-yl)oxycarbonylcarbamothioyl]carbamate
N,Nμ-Bis-tert-butoxycarbonylthiourea, N,Nμ-Di-(tert-butoxycarbonyl)thiourea
Thiodiimidotricarbonic acid ([(HO)C(O)NH]2C(S)), 1,5-bis(1,1-dimethylethyl) ester | [EINECS(EC#)]
215-888-7 | [Molecular Formula]
C11H20N2O4S | [MDL Number]
MFCD03093917 | [MOL File]
145013-05-4.mol | [Molecular Weight]
276.35 |
| Chemical Properties | Back Directory | [Melting point ]
131-135 °C(lit.)
| [density ]
1.152 | [storage temp. ]
Store at 0-5°C | [form ]
powder to crystal | [pka]
5.55±0.70(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C11H20N2O4S/c1-10(2,3)16-8(14)12-7(18)13-9(15)17-11(4,5)6/h1-6H3,(H2,12,13,14,15,18) | [InChIKey]
CSOJECDGWHHWRS-UHFFFAOYSA-N | [SMILES]
C(C)(C)(C)OC(=O)NC(=S)NC(=O)OC(C)(C)C |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white solid | [Uses]
N,N′-Di-Boc-thiourea (N,N′-di-Boc-substituted thiourea), also known as di-Boc-thiourea is a thioacylating agent for preparing thiocarbonyl compounds.
N,N′-Di-Boc-thiourea (di-Boc protected thiourea) may be used as a guanylating agent for the synthesis of guanidines, via guanylation of amines in the presence of Mukaiyama′s reagent as a promoter. | [Synthesis]
GENERAL METHOD: To an anhydrous tetrahydrofuran (120 mL) solution of thiourea (500 mg, 6.58 mmol) was slowly added a suspension of 60% sodium hydride in mineral oil (1184 mg, 29.61 mmol) at 0 °C under argon protection. The reaction mixture was stirred at room temperature for 30 min to ensure complete formation of the anion and subsequently cooled to 0°C. At this temperature, di-tert-butyl dicarbonate (3155 mg, 14.47 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight and then cooled to 0 °C again. Water (20 mL) was added slowly and dropwise to quench the reaction. The aqueous phase was extracted with ethyl acetate (3 x 50 mL). The combined organic phases were washed sequentially with brine (30 mL) and water (30 mL) and dried with anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, purification by cold hexane grinding gave N,N'-di-Boc-thiourea as a white crystalline solid (1019 mg, 90% yield). The product has a melting point of 120-122°C and a clear melting range.1H NMR (400 MHz, CDCl3) data: δ 1.57 (s, 18H, CH3, Boc), 3.93 (br s, 2H, NH). | [References]
[1] Chemistry - A European Journal, 2016, vol. 22, # 9, p. 3009 - 3018
[2] Tetrahedron Letters, 1992, vol. 33, # 40, p. 5933 - 5936
[3] Tetrahedron Letters, 2013, vol. 54, # 30, p. 3982 - 3984
[4] Patent: US2018/127358, 2018, A1. Location in patent: Paragraph 0202; 0203
[5] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4206 - 4213 |
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