Phosphorus sulfide (P2S5) → HCID 69224729, compound

HRID 2053395Notes

Reaction equation

HRID 2053395 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1O[N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:10]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:24]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[S:24][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:10]1

Participants

3

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 69224508HCID 69224508, compound

Product 1

HCID 69224729HCID 69224729, compound

Procedure

By the method of Asian. J. Chem., 2000, 12, 1358-1360, (±)-5-(2,6-dichlorophenyl)-3-(4-nitrophenyl)-2-isoxazoline can be treated with diphosphorus pentasulfide followed by aqueous quench to produce (±)-5-(2,6-dichlorophenyl)-3-(4-nitrophenyl)-2-isothiazoline. The nitrophenyl group can be reduced to the corresponding aniline with tin dichloride or iron powder and ammonium chloride. The aniline, in turn, can be treated with 2,2-dichloroacetyl chloride and triethylamine to yield (±)-2,2-dichloro-N-[4-[5-(2,6-dichlorophenyl)-3-(2-isothiazolinyl)]phenyl acetamide.

Workup

  1. customby aqueous quench

Sources & evidence

ORD record
ord-a70df284dafb4d8ea4480c1604994bd4
Source dataset
uspto-grants-2008_02
Patent number
US07326790B2

Reaction notes

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