3-Des(allylthio)Methyl-3-broMoMethyl Althiazide synthesis
- Product Name:3-Des(allylthio)Methyl-3-broMoMethyl Althiazide
- CAS Number:7181-60-4
- Molecular formula:C8H9BrClN3O4S2
- Molecular Weight:390.66
Yield:7181-60-4 100%
Reaction Conditions:
with hydrogen bromide in 1,4-dioxane;water at 100 - 120; for 0.333333 h;
Steps:
36.36a
To a mixture of 4-chloro-6-aminobenzene-1,3-disulfonamide (Aldrich, 15.2 g, 53.3 mmol) and bromoacetaldehyde dimethylacetal (6.3 mL, 9 g, 53.3 mmol) in anhydrous dioxane (45 mL) at 120° C., was added dropwise 48% hydrobromic acid in H20 (2 mL). The mixture was then heated at 100° C. for 20 minutes. The residue, after evaporation of the solvent, was diluted with water, the resultant precipitate was filtered, washed with water to give a sticky solid that was dissolved in EtOAc and dried over Na2SO4. The residue after evaporation of the solvent was recrystallized from EtOAc/hexane to give the title compound in quantitative yield as a white solid: mp 203-205° C.; 1H NMR (400 MHz, d6-DMSO) δ 8.16 (br s, 1H), 8.08 (br d, J=11.2Hz, 1H), 7.99 (s, 1H), 7.53 (br s, 2H), 7.05 (s, 1H), 4.88-5.03 (m, 1H), 3.65-3.72 (m, 2H); 13C NMR (100 MHz, d6-DMSO) δ 146.1, 134.7, 128.9, 125.3, 118.4, 117.4, 66.3, 31.5; Mass spectrum (API-TIS) m/z 387/389 (M-H), 407/409 (MNH4+); Anal. calcd for C8H9BrClN3O4S2. EtOAc: C, 25.41; H, 2.50; N, 10.46; Found: C, 25.35; H, 2.44; N, 10.46.
References:
US2006/189603,2006,A1 Location in patent:Page/Page column 48
