Benzoic acid, 3-cyano-, methyl ester → Methyl 3-carbamothioylbenzoate

HRID 1374274Notes

Reaction equation

HRID 1374274 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[N:11])[CH:5]=1.P([O-])(OCC)(SCC)=[S:14]>C1COCC1.O>[C:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([O:2][CH3:1])=[O:12])(=[S:14])[NH2:11]

Participants

5

Reactant 2

HCID 83554Benzoic acid, 3-cyano-, methyl esterHCID 53249491Diethyldithiophosphate

Product 1

HCID 23279244Methyl 3-carbamothioylbenzoateYield 102.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Preparation H1, Step 2: A solution of 2 g (0.01 mol) of methyl-3-cyanobenzoate in 32 ml of THF and 8 ml of water was charged with 2.3 g (0.012 mol) of diethyl dithiophosphate and heated at 80° C. for 24 h. THF was removed and the residue was taken in ethyl acetate. The extract was washed with water and concentrated to afford methyl 3-carbamothioylbenzoate (2.0 g) as a pale yellow solid.

Workup

  1. customPreparation H1, Step 2
  2. customTHF was removed
  3. washThe extract was washed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d1a6ab0fd0143cd87cdbd2315a8198e
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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