Water → 2-(Tert-butoxycarbonylamino)acetophenone thiosemicarbazone

HRID 604591Notes

Reaction equation

HRID 604591 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:19][NH:20][C:21]([NH2:23])=[S:22].O>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10](=[N:19][NH:20][C:21]([NH2:23])=[S:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 3037943Thiosemicarbazide HydrochlorideHCID 11230079tert-butyl N-(2-oxo-2-phenylethyl)carbamate

Product 1

HCID 866224902-(Tert-butoxycarbonylamino)acetophenone thiosemicarbazoneYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(tert-Butoxycarbonylamino)acetophenone (3.00 g) was dissolved in methanol (21.0 mL). To the solution was added an aqueous solution (water: 9.0 mL) of thiosemicarbazide hydrochloride (3.11 g, 24.4 mmol) at room temperature. After the mixture was stirred at the same temperature for 30 minutes, water (12.0 mL) was added, and the mixture was stirred at room temperature for 20 minutes and then at 0° C. for 1 hour. The deposited solid was collected by filtration and washed with cooled 50% aqueous methanol (20 mL). The resulting solid was dried at 40° C. under reduced pressure to give seed crystals of 2-(tert-butoxycarbonylamino)acetophenone thiosemicarbazone (3.56 g, yield: 95.1%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 minutes
  2. waitat 0° C. for 1 hour
  3. filtrationThe deposited solid was collected by filtration
  4. washwashed
  5. temperaturewith cooled 50% aqueous methanol (20 mL)
  6. customThe resulting solid was dried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-0dcd86ec0dd044999c2b38e0d4a15777
Source dataset
uspto-grants-2011_03
Patent number
US07910611B2

Reaction notes

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