Water ethanol → HCID 70530067, compound

HRID 1701944Notes

Reaction equation

HRID 1701944 reaction equation
C([O:3][C:4](=O)[C:5](=[O:23])[CH:6]([C:21]#[N:22])[CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[S:12][CH:13]=1)C.C([OH:27])C.O>CS(O)(=O)=O>[OH:23][C:5]1[C:4](=[O:3])[NH:22][C:21](=[O:27])[C:6]=1[CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[S:12][CH:13]=1

Participants

4

Reactant 2

HCID 19096565Water ethanolHCID 54036708HCID 54036708, compound

Product 1

HCID 70530067HCID 70530067, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

To 3-[2-(4-bromobiphenyl)thiazol-4-yl]butanenitrile (3.07 g., 0.01 mole) in dimethylformamide (30 ml.) is added diethyloxalate (1.74 g., 0.012 mole) and potassium t-butoxide (2.48 g., 0.022 mole). The mixture is stirred overnight. Following evaporation under vacuum to one-half volume, chloroform (300 ml.) is added, plus water (200 ml.), and the mixture acidified with conc. HCl to pH 2-3. The chloroform is separated and washed well with water. The combined aqueous fractions are extracted a second time with chloroform. The combined chloroform extracts on evaporation provide 2-oxo-3-cyano-5-[2-(4-bromophenyl)thiazol-4-yl]-pentanoic acid ethyl ester. The ester (1.97 g., 0.005 mole) is dissolved in methanesulfonic acid (70 ml.) and stirred overnight. To the mixture is added 80% ethanol-water (200 ml.). After standing for two hours the ethanol is partially removed by evaporation to give the title compound.

Workup

  1. waitAfter standing for two hours
  2. customthe ethanol is partially removed by evaporation

Sources & evidence

ORD record
ord-439f973d335a4264b2a675f7efe1b49c
Source dataset
uspto-grants-1983_04
Patent number
US04379791

Reaction notes

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