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

HRID 649103Notes

Reaction equation

HRID 649103 reaction equation
NC1C=C(C(F)(F)F)C=C(Cl)C=1OC1C=CC([N+]([O-])=O)=C(C=1)C(OC)=O.S(Cl)(Cl)=O.CS(N)(=O)=O.[CH3:36][S:37]([NH:40][C:41](=[O:63])[C:42]1[CH:47]=[C:46]([O:48][C:49]2[CH:54]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:52]=[CH:51][C:50]=2[Cl:59])[CH:45]=[CH:44][C:43]=1[N+]([O-])=O)(=[O:39])=[O:38]>N1C=CC=CC=1>[CH3:36][S:37]([NH:40][C:41](=[O:63])[C:42]1[CH:43]=[CH:44][CH:45]=[C:46]([O:48][C:49]2[CH:54]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:52]=[CH:51][C:50]=2[Cl:59])[CH:47]=1)(=[O:38])=[O:39]

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 72879MethanesulfonamideHCID 21287078Methyl 5-(2-amino-6-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoateHCID 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-2b42f58b0a8f4fe9a76680de0ac5b5c8
Source dataset
uspto-grants-1988_04
Patent number
US04738711

Reaction notes

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