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

HRID 868466Notes

Reaction equation

HRID 868466 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]>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

6

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 1

HCID 1049PyridineSolvent

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-3c8d4042321a43dea7d84804a6b8d860
Source dataset
uspto-grants-1988_10
Patent number
US04780128

Reaction notes

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