Phosphorus sulfide (P2S5) → 2-Amino-N-[(3,4-dichlorophenyl)methyl]benzenecarbothioamide

HRID 1639289Notes

Reaction equation

HRID 1639289 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21].C(=O)(O)[O-].[Na+]>O1CCOCC1>[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4](=[S:21])[NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 14458931HCID 14458931, compound

Product 1

HCID 144589332-Amino-N-[(3,4-dichlorophenyl)methyl]benzenecarbothioamideYield 47%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-N-(3,4-dichlorobenzyl)benzamide (3.5 g) and phosphorus pentasulfide (4.74 g) in dioxane (56 ml) was stirred at room temperature for 5 hours. The reaction mixture was poured into an aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water and dried. Evaporation of the solvent gave a residue, which was chromatographed on silica gel. Elution with chloroform followed by recrystallization from isopropyl ether gave 2-amino-N-(3,4-dichlorobenzyl)benzenecarbothioamide (1.56 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customEvaporation of the solvent
  5. customgave a residue, which
  6. customwas chromatographed on silica gel
  7. washElution with chloroform
  8. customfollowed by recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-8bbfd82aef0048e781103f4dd9a289d3
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Reaction notes

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