2-Bromothiazole → HCID 22106696, compound

HRID 1377555Notes

Reaction equation

HRID 1377555 reaction equation
C([Li])CCC.Br[C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[C:12]([C:15]1[S:16][CH:17]=[CH:18][N:19]=1)(=[O:14])[CH3:13].C(=O)([O-])O.[Na+]>C(OCC)C>[S:8]1[CH:9]=[CH:10][N:11]=[C:7]1[C:12]([C:15]1[S:16][CH:17]=[CH:18][N:19]=1)([OH:14])[CH3:13]

Participants

6

Reactant 4

HCID 764302-BromothiazoleHCID 516892Sodium BicarbonateHCID 5201082-AcetylthiazoleHCID 178418339Butyllithium

Product 1

HCID 22106696HCID 22106696, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyllithium (2.5M solution in hexanes, 17.3 ml) was added dropwise to a stirred solution of 2-bromothiazole (6.5 g) in anhydrous diethyl ether (40 ml) at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 2-acetylthiazole (5 g) in diethyl ether (10 ml) was added dropwise. After a further 1 hour, the mixture was allowed to warm to room temperature. After 1 hour, saturated aqueous sodium hydrogen carbonate solution was added and the organic phase was separated. Further processing in the usual fashion then gave the title compound.

Workup

  1. waitAfter a further 1 hour
  2. waitAfter 1 hour
  3. customthe organic phase was separated

Sources & evidence

ORD record
ord-22aed2456d1746629ac0775e2b6586ed
Source dataset
uspto-grants-1997_09
Patent number
US05665747

Reaction notes

Loading…