Hydrochloric Acid → HCID 178513777, compound

HRID 1712126Notes

Reaction equation

HRID 1712126 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]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 4311764Sodium borohydrideHCID 178510544HCID 178510544, compound

Product 1

HCID 178513777HCID 178513777, compoundYield 81%

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) δ 13.0 (s, 1H), 11.0-10.9 (bs, 1H), 10.3 (s, 1H), 7.47 (1.2H, J=6.8 Hz), 7.37-7.30 (m, 4H) ppm; MS (APCI, m/z): 296 [M+H]+.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in 10 mL of ethanol at 0° C.
  6. stirringAfter stirring for 30 minutes
  7. extractionextracted into ethyl acetate
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0537ce9a0b4b4db5bc1b7eedf65fa8fe
Source dataset
uspto-grants-2010_09
Patent number
US07790902B2

Reaction notes

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