Acetic Anhydride → HCID 14305461, compound

HRID 1607693Notes

Reaction equation

HRID 1607693 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:17]=[CH:16][C:10]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:9]([O:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])[CH:8]=2)[N:6]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>>[C:27]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:17]=[CH:16][C:10]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:9]([O:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])[CH:8]=2)[N:6]=1)(=[O:29])[CH3:28]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 10453409HCID 10453409, compound

Product 1

HCID 14305461HCID 14305461, compound

Procedure

A solution of 4'-(2-amino-4-thiazolyl)-2'-(2,4-difluorophenoxy)methanesulfonanilide (1.2 g) in acetic anhydride (3 ml) was stirred for 30 minutes at 80° C. The mixture was concentrated, and then evaporated with xylene and ethanol. The residue (1.4 g) was purified by column chromatography on silica gel (30 g) eluting with a mixture of toluene and ethyl acetate (1:1), and recrystallized from ethanol to afford pale brown crystals of 4'-(2-acetamido-4-thiazolyl)-2'-(2,4-difluorophenoxy)methanesulfonanilide (0.82 g).

Workup

  1. concentrationThe mixture was concentrated
  2. customevaporated with xylene and ethanol
  3. customThe residue (1.4 g) was purified by column chromatography on silica gel (30 g)
  4. washeluting with a mixture of toluene and ethyl acetate (1:1)
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-61d753ecb3fa46d29be6bae5af8eb1ba
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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