Water → methyl 2-oxo-3-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl-methyl)-2,3-dihydrobenzoxazole-5-carboxylate

HRID 655319Notes

Reaction equation

HRID 655319 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[NH2:23])[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]1=[O:19].[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25].O>C1COCC1>[O:19]=[C:7]1[N:6]([CH2:5][C:4]2[CH:20]=[CH:21][C:22]3[NH:23][C:24](=[O:25])[NH:1][C:2]=3[CH:3]=2)[C:10]2[CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 58486039Methyl 3-(3,4-diaminobenzyl)-2-oxo-2,3-dihydrobenzoxazole-5-carboxylate

Product 1

HCID 59564730methyl 2-oxo-3-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl-methyl)-2,3-dihydrobenzoxazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.1 g (3.5 mmol) of methyl 3-(3,4-diaminobenzyl)-2-oxo-2,3-dihydrobenzoxazole-5-carboxylate and 626 mg (3.9 mmol) of 1,1′-carbonyldiimidazole are stirred at room temperature for 24 h in 10 ml of THF. The reaction mixture is added to 150 ml of water, and the resultant precipitate is filtered off with suction and dried in vacuo; product: 1.1 g; ESI: 340 (M+H).

Workup

  1. filtrationthe resultant precipitate is filtered off with suction
  2. customdried in vacuo

Sources & evidence

ORD record
ord-3ab14bf4043b40ea86ae493e65648ca6
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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