Ammonia → HCID 69223034, compound

HRID 2053392Notes

Reaction equation

HRID 2053392 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C: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)[CH:10]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:24].N>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C: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)[CH:10]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 14817Phosphorus sulfide (P2S5)HCID 69224616HCID 69224616, compound

Product 1

HCID 69223034HCID 69223034, compound

Procedure

By the method of Tetrahedron, 1992, 48, 8127-8142 the substance 5-(2,6-dichlorophenyl)-3-(4-nitrophenyl)isoxazole can be treated with diphosphorus pentasulfide followed by aqueous or ethanolic ammonia quench to produce 5-(2,6-dichlorophenyl)-3-(4-nitrophenyl)isothiazole. The nitrophenyl group can be reduced to the corresponding aniline with tin (II) dichloride or iron powder and ammonium chloride. This aniline can then be treated with 2,2-dichloroacetyl chloride and triethylamine to yield 2,2-dichloro-N-[4-[5-(2,6-dichlorophenyl)-3-isothiazolyl]phenyl]acetamide.

Workup

  1. customquench

Sources & evidence

ORD record
ord-c4f95b3103884cf58b525cf67c4946a7
Source dataset
uspto-grants-2008_02
Patent number
US07326790B2

Reaction notes

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