Water → HCID 24886662, compound

HRID 1785476Notes

Reaction equation

HRID 1785476 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1.[H-].[Na+].[CH2:16]([O:18][C:19]([C:21]1[S:25][C:24](Cl)=[N:23][C:22]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:20])[CH3:17].O>CN1C(=O)CCC1>[CH2:16]([O:18][C:19]([C:21]1[S:25][C:24]([N:9]2[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[CH:10][C:6]=3[N:7]=[CH:8]2)=[N:23][C:22]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:20])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6012215,6-DimethoxybenzimidazoleHCID 13041816Ethyl 2-chloro-4-phenyl-1,3-thiazole-5-carboxylate

Product 1

HCID 24886662HCID 24886662, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

5,6-Dimethoxybenzimidazole (470 mg, 2.64 mmol) was added to a suspension of NaH (60% in mineral oil, 112 mg, 2.8 mmol) in NMP (5 ml) at <5° C. The mixture was stirred for 20 min, then a solution of 2-chloro-4-phenylthiazole-5-carboxylic acid ethyl ester (589 mg, 2.2 mmol) in NMP (1.5 ml) was added over 2-3 min. The mixture was stirred 2.5 hrs at RT. Water (15 ml) was added and stirred for 20 min. Solid was collected by filtration to provide the product 2-(5,6-dimethoxy-benzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid ethyl ester (753 mg. Yield 84%). 1H-NMR (300 MHz, CDCl3) 8.44(s, 1H); 7.87-7.90(m, 2H); 7.72(2, 1H); 7.44-7.49(m, 3H); 7.30(s, 1H); 4.32(q, J=Hz, 2H); 3.98(s, 3H); 3.97(s, 3H); 1.33(t, J=Hz, 3H). MS M/z 410(M+1).

Workup

  1. stirringThe mixture was stirred 2.5 hrs at RT
  2. stirringstirred for 20 min
  3. filtrationSolid was collected by filtration

Sources & evidence

ORD record
ord-0af8c32461614a67a44ada3a3898c093
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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