Imidazole → 3-(1H-imidazol-1-yl)propanoic acid

HRID 1249499Notes

Reaction equation

HRID 1249499 reaction equation
ClC1C=CC(O)=CC=1.BrCC(SC1C(Cl)=CC=CC=1Cl)C[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.Br[CH2:28][CH2:29][C:30]([OH:32])=[O:31].N1C=CN=C1>>[N:13]1([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

5

Reactant 4

HCID 795ImidazoleHCID 46844-ChlorophenolHCID 115533-Bromopropionic acidHCID 202235331-Bromo-2-(2,6-dichlorophenylthio)-3-(1-imidazolyl)propane

Product 1

HCID 27947183-(1H-imidazol-1-yl)propanoic acid

Procedure

A mixture of 12.9 g of p-chlorophenol, 36.6 g of 1-bromo-2-(2,6-dichlorophenylthio)-3-(1-imidazolyl)propane [obtainable by reaction of 3-bromopropionic acid with imidazole to give 3-(1-imidazolyl)propionic acid, bromination to give 2-bromo-3-(1-imidazolyl)propionic acid, reaction with Na 2,6-dichlorothiophenolate to give 2-(2,6-dichlorophenylthio)-3-(1-imidazolyl)propionic acid, reduction with LiAlH4 to give the corresponding alcohol, and reaction with PBr3 ], 8 g of NaOH and 400 ml of ethanol is heated at 100° for 10 hours. The mixture is evaporated, worked up as usual and Ia of m.p. 175°-177° is obtained.

Sources & evidence

ORD record
ord-75b4176ac4a84027842706d3df1a3eb6
Source dataset
uspto-grants-1986_12
Patent number
US04632933

Reaction notes

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