Benzimidazole → HCID 69355215, compound

HRID 350703Notes

Reaction equation

HRID 350703 reaction equation
Cl[C:2]1[S:3][C:4]([CH:10]=O)=[C:5]([CH:7]([CH3:9])[CH3:8])[N:6]=1.C(OP([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(OCC)=O)C.[H-].[Na+].[N:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[NH:30][CH:29]=1>O.CN(C)C=O>[N:28]1([C:2]2[S:3][C:4](/[CH:10]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:5]([CH:7]([CH3:8])[CH3:9])[N:6]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=[CH:29]1

Participants

7

Reactant 4

HCID 5798BenzimidazoleHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride2×HCID 23061732HCID 23061732, compound

Product 1

HCID 69355215HCID 69355215, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-4-isopropyl-5-thiazolecarbaldehyde (2.0 g), ethyl diethylphosphonoacetate (2.47 g), sodium hydride (0.44 g) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 1 hr. Benzimidazole (1.54 g) and sodium hydride (0.44 g) were added to the reaction mixture and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was poured into water, the precipitated crystals were collected by filtration and washed with water. Recrystallization from acetone-hexane gave ethyl (2E)-3-[2-(1H-benzimidazol-1-yl)-4-isopropyl-5-thiazolyl]propenoate (3.01 g, 84%) as a pale-yellow prism crystal. melting point: 229–230° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-3136b4fd38184e13993e6b8b858cdd77
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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