Acetic Acid → Methyl 4-carbamothioylbenzoate

HRID 1742397Notes

Reaction equation

HRID 1742397 reaction equation
C(O)(=[S:3])C.[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)#[N:6].C(O)(=O)C>C(O)(C)C.O>[C:11]([C:10]1[CH:15]=[CH:16][C:7]([C:5](=[S:3])[NH2:6])=[CH:8][CH:9]=1)([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 70791Methyl 4-cyanobenzoateHCID 178418634HCID 178418634, compound

Product 1

HCID 11401319Methyl 4-carbamothioylbenzoateYield 77.7%

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

130 g (1.7 moles) of thioacetic acid, 50 g (0.3 mole) of methyl 4-cyanobenzoate and 12 ml of glacial acetic acid were stirred for 2 hours at 80° C. The mixture was allowed to cool, 200 ml of 1:1 isopropanol/water was added, the mixture was stirred for a short time and the crystals formed were filtered off under suction. 45.5 g of 4-carbomethoxybenzothiamide of melting point 188°-190° C. were obtained in this manner.

Workup

  1. temperatureto cool
  2. customthe crystals formed
  3. filtrationwere filtered off under suction

Sources & evidence

ORD record
ord-a24abb6e0f734c819b6ca26f83e9ee51
Source dataset
uspto-grants-1994_08
Patent number
US05338749

Reaction notes

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