Ammonium Chloride → Methyl 3-[2-(thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]-5-phenylbenzoate

HRID 2228022Notes

Reaction equation

HRID 2228022 reaction equation
CC(C)([O-])C.[K+].[N:7]1([CH2:12][C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=O)[CH:11]=[CH:10][N:9]=[CH:8]1.[Br-].[CH3:21][O:22][C:23]([C:25]1[CH:26]=[C:27]([CH:48]=[C:49]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:50]=1)[CH2:28][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:24].C1OCCOCCOCCOCCOCCOC1.[Cl-].[NH4+]>ClCCl>[S:16]1[CH:17]=[CH:18][N:19]=[C:15]1[C:13]([CH2:12][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1)=[CH:28][C:27]1[CH:26]=[C:25]([CH:50]=[C:49]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:48]=1)[C:23]([O:22][CH3:21])=[O:24]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 223249842-(Imidazol-1-yl)-1-(thiazol-2-yl)-ethanoneHCID 23665647Potassium tert-butoxideHCID 865903393-Methoxycarbonyl-5-phenylbenzyl triphenylphosphonium bromide

Product 1

HCID 54338365Methyl 3-[2-(thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]-5-phenylbenzoateYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Potassium tert-butoxide (1.05 g; 9.39 mmnol) was added to mixture of thiazol-2-yl imidazol-1-ylmethyl ketone (1.20 g; 6.25 mmol), 3-methoxycarbonyl-5-phenylbenzyl triphenyl phosphonium bromide (5.3 g; 9.39 mmol) and 18-crown-6 (0.08 g; 0.24 mmol) in dichloromethane (20 ml), at −60° C. under an argon atmosphere. After stirring overnight, at room temperature, the resulting mixture was treated with a saturated aqueous solution of ammonium chloride purified by flash chromatography eluting with dichloromethane/ethanol (95/5) to give methyl 3-[2-(thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]-5-phenylbenzoate (Z isomer). Yield=39%.

Workup

  1. custompurified by flash chromatography
  2. washeluting with dichloromethane/ethanol (95/5)

Sources & evidence

ORD record
ord-a8a638315bdc4150a28f4a1e17bacb66
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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