Pyridine → 4-Diacetylamino-2-bromothiazole

HRID 26199Notes

Reaction equation

HRID 26199 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 10 g, 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; N, 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-47f7e7441b0743cd9732fce06a051fe2
Source dataset
uspto-grants-1979_04
Patent number
US04148904

Reaction notes

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