Ethyl isothiocyanatoformate → HCID 178473561, compound

HRID 1296714Notes

Reaction equation

HRID 1296714 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][N:3]=1.[CH2:13]([O:15][C:16]([N:18]=[C:19]=[S:20])=[O:17])[CH3:14]>C1(C)C=CC=CC=1>[C:7]1([C:5]2[CH:6]=[C:2]([NH:1][C:19]([NH:18][C:16](=[O:17])[O:15][CH2:13][CH3:14])=[S:20])[NH:3][N:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 1366553-Amino-5-phenylpyrazole

Product 1

HCID 178473561HCID 178473561, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a cold (0° C.) solution of 3-amino-5-phenylpyrazole (10.0 g, 62.8 mmol) in toluene (100 mL) was added ethoxycarbonyl isothiocyanate (8.3 mL, 70 mmol) dropwise via a pressure equalizing funnel. Upon complete addition, the cold bath was removed and the resulting solution was stirred at room temperature for 15hours, at which time a heavy white precipitate had formed. The precipitate was collected by filtration and dried to give ethyl [(3-phenyl-1H-pyrazol-5-yl)amino]carbothioylcarbamate (11 g, 60%) as a white solid. 1H-NMR (DMSO-d6): δ 13.25 (s, 1H), 12.06 (s, 1H), 11.40 (s, 1H), 7.75 (d, 2H), 7.5–7.3 (m, 4H), 4.25 (q, 2H), 1.29 (t, 3H); MS m/z 291 (M+1).

Workup

  1. additionUpon complete addition
  2. customthe cold bath was removed
  3. customhad formed
  4. filtrationThe precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-f84d847e5d8843a58fe53ad4733cecc6
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

Loading…