Hydrochloric Acid → HCID 53971735, compound

HRID 1601330Notes

Reaction equation

HRID 1601330 reaction equation
O=[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][CH2:4][CH2:5][O:6][C:7](=[O:15])[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.O.[CH3:24][NH:25][C:26](=[S:29])[NH:27][NH2:28]>CO>[CH3:24][NH:25][C:26]([NH:27][N:28]=[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][CH2:4][CH2:5][O:6][C:7]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:15])=[S:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723853N-MethylhydrazinecarbothioamideHCID 53964867HCID 53964867, compound

Product 1

HCID 53971735HCID 53971735, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenyl-carbamic acid 4-oxo-4-phenyl-butyl ester (2.80 g, 9.88 mmol), prepared in the previous step, was suspended in 60 ml of methanol and the mixture warmed to dissolve the solid. While still warm 2.7 ml of 1 N HCl, 2.7 ml of water and 4-methyl-3-thiosemicarbazide (1.04 g, 9.92 mmol) were added and the reaction stirred under nitrogen for 21 hours. The solid formed was removed by filtration and dried under high vacuum to give the title compound (3.07 g, 84%) as a white solid, mp 155-157° C.

Workup

  1. temperaturethe mixture warmed
  2. dissolutionto dissolve the solid
  3. customThe solid formed
  4. customwas removed by filtration
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-f5b307e4ca5446f287622aee5455fe84
Source dataset
uspto-grants-1999_11
Patent number
US05977170

Reaction notes

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