Hydrochloric Acid → HCID 178513777, compound
Reaction equation
[C:1]1([O:7][C:8](=[O:18])[NH:9][C:10]2[S:14][N:13]=[C:12]([SH:15])[C:11]=2[C:16]#[N:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C1C=C(C)C=C(C(C)(C)C)C=1[OH:34])(C)(C)C.S(=O)(=O)(O)O.[BH4-].[Na+].Cl>>[C:1]1([O:7][C:8](=[O:18])[NH:9][C:10]2[S:14][N:13]=[C:12]([SH:15])[C:11]=2[C:16](=[O:34])[NH2:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Procedure
A mixture of (4-cyano-3-mercapto-isothiazol-5-yl)-carbamic acid phenyl ester (0.70 g, 2.5 mmol), 2,6-di-tert-butyl-4-methylphenol (BHT) (one crystal) and concentrated sulfuric acid (3 mL) was stirred for 18 hours at room temperature. The mixture was diluted with ice water, extracted 3× with ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in 10 mL of ethanol at 0° C. and was treated with 0.096 g (2.5 mmol) of NaBH4. After stirring for 30 minutes, the mixture was acidified with 1 M HCl, extracted into ethyl acetate, dried over Na2SO4, filtered and concentrated in vacuo, affording 0.60 g (81%) of (4-carbamoyl-3-mercapto-isothiazol-5-yl)-carbamic acid phenyl ester as a yellow solid. 1H NMR (400 MHz, acetone-d6) δ13.0 (s, 1H), 11.0-10.9 (bs, 1H), 10.3 (s, 1H), 7.47 (t, 2H, J=6.8 Hz), 7.37-7.30 (m, 4H), ppm; MS (APCI, m/z): 296 [M+H]30 .
Workup
- extractionextracted 3× with ethyl acetate
- dry with materialthe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in 10 mL of ethanol at 0° C.
- stirringAfter stirring for 30 minutes
- extractionextracted into ethyl acetate
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2aa8d1bb4254467691d597405d7dfcb6
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235764B1
Reaction notes
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