Hydrochloric Acid → 2-Chloro-N-[3-chloro-4-(trifluoromethyl)benzyl]-4-[(1,2,4-thiadiazol-5-ylamino)sulfonyl]benzamide

HRID 1808161

Reaction equation

HRID 1808161 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:23](Cl)(=[O:25])=[O:24])[CH:5]=[CH:6][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14]([Cl:22])[CH:13]=1)=[O:9].[NH2:27][C:28]1[S:32][N:31]=[CH:30][N:29]=1.Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([S:23]([NH:27][C:28]2[S:32][N:31]=[CH:30][N:29]=2)(=[O:25])=[O:24])[CH:5]=[CH:6][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14]([Cl:22])[CH:13]=1)=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 2902745-Amino-1,2,4-thiadiazoleHCID 577321163-Chloro-4-({[3-chloro-4-(trifluoromethyl)benzyl]amino}carbonyl)benzenesulfonyl chloride

Product 1

HCID 577321642-Chloro-N-[3-chloro-4-(trifluoromethyl)benzyl]-4-[(1,2,4-thiadiazol-5-ylamino)sulfonyl]benzamide

Procedure

The title compound was prepared from 3-chloro-4-({[3-chloro-4-(trifluoromethyl)benzyl]amino}carbonyl)benzenesulfonyl chloride (Preparation 38) and 5-amino-1,2,4-thiadiazole in following Method H described for Example 6. The reaction mixture was added to 2M HCl, extracted into ethyl acetate, dried over sodium sulphate, filtered and evaporated. The crude material was purified by column chromatography eluting with DCM:MeOH:AcOH (95:5:0.5) to yield the title compound.

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by column chromatography
  6. washeluting with DCM:MeOH:AcOH (95:5:0.5)

Sources & evidence

ORD record
ord-e94beae2b86e4b7d8687e656e2ab7732
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Linked notes

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