Water → methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylate

HRID 2386802Notes

Reaction equation

HRID 2386802 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[NH2:24])[C:17]([O:19][CH3:20])=[O:18].O>C1COCC1>[CH3:20][O:19][C:17]([C:16]1[CH:21]=[CH:22][C:23]2[NH:24][C:1](=[O:2])[NH:13][C:14]=2[CH:15]=1)=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 10352553methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,1′-carbonyldiimidazole (5 g) in THF (20 ml) was added to a solution of methyl 3,4-diaminobenzoate (CAS Reg. No. 36692-49-6, 5 g) in THF (50 ml). The mixture was stirred at room temperature for 2 h. Water (150 ml) was added. The mixture was filtered and the residue dried to give the title compound (5.6 g) as a light yellow powder. MS (m/e, ISP neg. ion)=191.2 [M−H+].

Workup

  1. filtrationThe mixture was filtered
  2. customthe residue dried

Sources & evidence

ORD record
ord-c153e845205c4507857cfe8722a6107a
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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