Methyl benzimidate hydrochloride → HCID 18700003, compound

HRID 2288618Notes

Reaction equation

HRID 2288618 reaction equation
Cl.CO[C:4](=N)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:12]1([CH2:19][C:20]2[S:21][C:22]([C:25]([NH:27][NH2:28])=[O:26])=[CH:23][CH:24]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>N1C=CC=CC=1>[C:5]1([C:4]2[O:26][C:25]([C:22]3[S:21][C:20]([CH2:19][N:12]4[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]4)=[CH:24][CH:23]=3)=[N:27][N:28]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 5743287Methyl benzimidate hydrochlorideHCID 55213626HCID 55213626, compound

Product 1

HCID 18700003HCID 18700003, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

687 mg (4.0 mmol) of methylbenzoimidate hydrochloride was added to 7 ml of pyridine solution containing 507 mg (2.0 mmol) of 2-(hexahydro-1H-azepin-1-yl)methylthiophene-5-carboxylic acid hydrazide, and the mixture was heated under reflux for 4 hours. The reaction solution was concentrated, chloroform was added to the resulting residue, followed by washing with water and drying over anhydrous magnesium sulfate. The solvent was evaporated and the resulting residue was purified by a silica gel column chromatography to give 110 mg of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe reaction solution was concentrated
  4. additionchloroform was added to the resulting residue
  5. washby washing with water
  6. dry with materialdrying over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-c0c25a0750784feea72de50ebe2a4fdf
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

Loading…