Methyl 4-cyanobenzoate → Methyl 4-carbamothioylbenzoate

HRID 902775Notes

Reaction equation

HRID 902775 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1.P([O-])(OCC)(SCC)=[S:14]>O>[NH2:11][C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:12])=[CH:5][CH:6]=1)=[S:14]

Participants

4

Reactant 2

HCID 70791Methyl 4-cyanobenzoateHCID 53249491Diethyldithiophosphate

Product 1

HCID 11401319Methyl 4-carbamothioylbenzoateYield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl-4-cyanobenzoate (5.0 g, 0.031 mol) and diethyl dithiophosphate (11.5 g, 0.062 mol) in water (100 mL) was stirred overnight at 80° C. under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperatures and the solid was filtered and washed with water (100 mL). The solid was then dried in vacuo at 40° C. to give the crude product (4.74 g, 78%).

Workup

  1. temperatureto cool to ambient temperatures
  2. filtrationthe solid was filtered
  3. washwashed with water (100 mL)
  4. customThe solid was then dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-7c5337ca7d664326b1759009786a75df
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Reaction notes

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