Ethyl formate → HCID 178491157, compound

HRID 1934674Notes

Reaction equation

HRID 1934674 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:10]=2[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)=[O:12])[CH2:4][CH2:3]1.[CH:32](OCC)=[O:33]>CN(C)C=O>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][CH3:22])[CH2:14][NH:13][C:11](=[O:12])[C:10]1[CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[CH:27]=[CH:28][C:9]=1[NH:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([NH:1][CH:32]=[O:33])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 178491154HCID 178491154, compound

Product 1

HCID 178491157HCID 178491157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(trans-4-aminocyclohexyl)amino]-N-(3,4-dimethoxybenzyl)-5nitrobenzamide (10 g) in dimethylformamide (60 mL) was added ethyl formate (200 mL), and the mixture was heated for 8 hours under reflux. The mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of chloroform and methanol (20: 1). The obtained product was recrystallized from ethanol to give N-(3,4-dimethoxybenzyl)-2-[(trans-4-formamidocyclohexyl)amino]-5-nitrobenzamide as yellow crystals (7.21 g).

Workup

  1. temperaturethe mixture was heated for 8 hours
  2. temperatureunder reflux
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by a silica gel column chromatography
  8. washeluting with a mixture of chloroform and methanol (20: 1)
  9. customThe obtained product was recrystallized from ethanol

Sources & evidence

ORD record
ord-dfceb20c3c674344911241a0ef18b4bb
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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