Thionyl Chloride → N-methane-sulphonyl-3-(2-chloro-5-trifluoromethylphenoxy)benzamide

HRID 358198Notes

Reaction equation

HRID 358198 reaction equation
ClC1C=CC(C(F)(F)F)=CC=1OC1C=C(C=CC=1)C(O)=O.S(Cl)(Cl)=O.CS(N)(=O)=O.[CH3:31][S:32]([NH:35][C:36](=[O:58])[C:37]1[CH:42]=[C:41]([O:43][C:44]2[CH:49]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:47]=[CH:46][C:45]=2[Cl:54])[CH:40]=[CH:39][C:38]=1[N+]([O-])=O)(=[O:34])=[O:33]>C(OCCCC)(=O)C.N1C=CC=CC=1>[CH3:31][S:32]([NH:35][C:36](=[O:58])[C:37]1[CH:38]=[CH:39][CH:40]=[C:41]([O:43][C:44]2[CH:49]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:47]=[CH:46][C:45]=2[Cl:54])[CH:42]=1)(=[O:33])=[O:34]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 72879MethanesulfonamideHCID 193892503(2-Chloro-5-trifluoromethylphenoxy)benzoic acidHCID 212870795-[2-chloro-5-(trifluoromethyl)phenoxy]-N-methanesulfonyl-2-nitrobenzamide

Product 1

HCID 21287082N-methane-sulphonyl-3-(2-chloro-5-trifluoromethylphenoxy)benzamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 31272Butyl AcetateSolvent

Procedure

The acid from (b) (0.8 g) was treated with thionyl chloride followed by methanesulphonamide and pyridine as described in paragraph (d) above for compound 32. The product was recrystallised from a mixture of ether and petroleum (b.p. 40°-60°) to give compound 31 with a melting point of 132°-133°.

Workup

  1. customThe product was recrystallised from a mixture of ether and petroleum (b.p. 40°-60°)

Sources & evidence

ORD record
ord-6cecb5148a6f4006803937a0c0adac48
Source dataset
uspto-grants-1984_08
Patent number
US04465508

Reaction notes

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