Isobutyryl chloride → 2-Bromo-4-isobutyramidothiazole

HRID 2052211Notes

Reaction equation

HRID 2052211 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].Br.[NH2:8][C:9]1[N:10]=[C:11]([Br:14])[S:12][CH:13]=1.C([O-])(=O)C.[Na+]>N1C=CC=CC=1>[Br:14][C:11]1[S:12][CH:13]=[C:9]([NH:8][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[N:10]=1

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 517045Sodium AcetateHCID 202940412-Bromo-1,3-thiazol-4-amine--hydrogen bromide (1/1)

Product 1

HCID 203771722-Bromo-4-isobutyramidothiazoleYield 20%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of isobutyryl chloride (4.15 ml., 40 mM) in pyridine (50 ml.) was cooled to 0° C. and treated portionwise with 4-amino-2-bromothiazole hydrobromide (7.8 g, 30 mM). After stirring for 1 h. the reaction mixture was poured onto 20% aqueous sodium acetate solution (500 ml) and extracted with chloroform (3×200 ml.). The combined organic layers were dried and the solvents removed under reduced pressure to yield an oil which eventually crystallised. Recrystallisation from 60°-80° petroleum ether gave the title compound (2 g, 20%). mp: 95° (Found: C, 34.1; H, 3.8; N, 11.3. C7H9BrN2OS requires C, 33.7; H, 3.6; N, 11.2%).

Workup

  1. extractionextracted with chloroform (3×200 ml.)
  2. customThe combined organic layers were dried
  3. customthe solvents removed under reduced pressure
  4. customto yield an oil which
  5. customeventually crystallised
  6. customRecrystallisation from 60°-80° petroleum ether

Sources & evidence

ORD record
ord-6476795a60ec4898a9a3164ac871ff09
Source dataset
uspto-grants-1980_01
Patent number
US04183854

Reaction notes

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