Pyridine → 4-Diacetylamino-2-bromothiazole

HRID 2052214Notes

Reaction equation

HRID 2052214 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7]([Br:10])[S:8][CH:9]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>>[C:1]([N:4]([C:17](=[O:19])[CH3:18])[C:5]1[N:6]=[C:7]([Br:10])[S:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 202940434-Acetamido-2-bromo-thiazole

Product 1

HCID 203771654-Diacetylamino-2-bromothiazoleYield 10.7%

Procedure

A solution of 4-acetylamino-2-bromothiazole 10g, prepared as described in Example 1, in acetic anhydride (100 ml) and pyridine (35 ml) was stirred at 100° C. for 24 hours. The reaction mixture was cooled and the excess acetic anhydride and pyridine removed in vacuo, and the residue was re-evaporated three times with toluene. The residue was purified by column chromatography using silica gel and eluting with chloroform, and recrystallised from hexane to give the title compound (1.2 g) m.p. 63°-65° C. (Found: C, 32.1; H, 2.8; H, 10.6 C7H7BrN2O2S requires C, 32.0; H, 2.7; N, 10.7%)

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe excess acetic anhydride and pyridine removed in vacuo
  3. customthe residue was re-evaporated three times with toluene
  4. customThe residue was purified by column chromatography
  5. washeluting with chloroform
  6. customrecrystallised from hexane

Sources & evidence

ORD record
ord-4a82443f8bda4e489044999ff724092f
Source dataset
uspto-grants-1980_01
Patent number
US04183854

Reaction notes

Loading…