Water → HCID 69513078, compound

HRID 1295830Notes

Reaction equation

HRID 1295830 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH2:19])[C:6]([NH:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[CH:7][CH:8]=1.[C:20](N1C=CN=C1)(N1C=CN=C1)=[O:21].O>O1CCCC1>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]([C:10]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=3[O:17][CH3:18])[C:20](=[O:21])[NH:19][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 69512400HCID 69512400, compound

Product 1

HCID 69513078HCID 69513078, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-N1-(5-chloro-2-methoxy-phenyl)-benzene-1,2-diamine hydrochloride (6.3 g, 20 mmol) in tetrahydrofurane (70 ml) was added carbonyldiimidazole (9 g 55 mmol). The reaction mixture was stirred at 60° C. overnight, poured into water (app. 200 ml) and extracted with ethylacetate, and the organic phase was washed with brine and evaporated to an oil. The title compound was crystallized from toluene.

Workup

  1. extractionextracted with ethylacetate
  2. washthe organic phase was washed with brine
  3. customevaporated to an oil
  4. customThe title compound was crystallized from toluene

Sources & evidence

ORD record
ord-d0752d69c8bc46b4853f87fe876ef812
Source dataset
uspto-grants-2007_07
Patent number
US07244756B2

Reaction notes

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