Hydrochloric Acid → HCID 69595574, compound

HRID 844835Notes

Reaction equation

HRID 844835 reaction equation
C(OC([NH:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([S:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[C:11]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:10]=1)=O)(C)(C)C.[ClH:31]>C(OCC)C>[ClH:31].[NH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([S:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[C:11]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9889937HCID 9889937, compound

Product 1

HCID 69595574HCID 69595574, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Toluene-4-thiosulfonic acid S-(4-tert-butoxycarbonylamino-2-tert-butyl-5-methylphenyl) ester (33a) (70.0 grams, 156 mmol) was dissolved in ethyl ether (500 mL). Anhydrous hydrogen chloride gas was bubbled through the solution while maintaining the temperature between 12 and 17° C. A precipitate formed after about 1 hour. The hydrogen chloride gas treatment was continued for an additional 3 hours at 17-25° C. The resulting mixture was allowed to stir overnight at room temperature and filtered and the product washed with ethyl ether (1.2) and vacuum dried at 40° C. to give 59 g (0.15 mmol, 96% yield) toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methylphenyl) ester hydrochloride (29b): mp: 169° C. (dec); Assay (HPLC): 99.8 area %.

Workup

  1. customAnhydrous hydrogen chloride gas was bubbled through the solution
  2. temperaturewhile maintaining the temperature between 12 and 17° C
  3. customA precipitate formed after about 1 hour
  4. filtrationfiltered
  5. washthe product washed with ethyl ether (1.2) and vacuum
  6. customdried at 40° C.

Sources & evidence

ORD record
ord-f6fecacbfcbf4792aa4cd5654b299d32
Source dataset
uspto-grants-2002_04
Patent number
US06380400B1

Reaction notes

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