Dimethylformamide → HCID 22405260, compound

HRID 441218Notes

Reaction equation

HRID 441218 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([OH:8])=O.CN(C)C=O.C(Cl)(=O)C(Cl)=O.[NH:26]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[NH:30][CH2:29][CH2:28][C:27]1=[O:37]>ClCCl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([N:30]1[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[NH:26][C:27](=[O:37])[CH2:28][CH2:29]1)=[O:8]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 787643-Methoxy-4-nitrobenzoic acidHCID 2237712,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Product 1

HCID 22405260HCID 22405260, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

To a solution of 3-methoxy-4-nitrobenzoic acid (800 mg) and catalytic amount of N,N-dimethylformamide in dichloromethane (8 ml) was added oxalyl chloride (0.7 ml) at 0° C. and the solution was stirred at ambient temperature for 30 minutes followed by the removal of solvents to give a crude acid chloride. To a solution of 1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (658 mg) and triethylamine (821 mg) in dichloromethane (4 ml) was added a solution of the above acid chloride in dichloromethane (4 ml) at ambient temperature and the mixture was stirred at ambient temperature for 1 hour. The resultant mixture was filtered and the solid was washed with water and diethyl ether to give 5-(3-methoxy-4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (1.29 g) as a colorless prisms.

Workup

  1. customfollowed by the removal of solvents
  2. customto give a crude acid chloride
  3. stirringthe mixture was stirred at ambient temperature for 1 hour
  4. filtrationThe resultant mixture was filtered
  5. washthe solid was washed with water and diethyl ether

Sources & evidence

ORD record
ord-4f336c2b673b4b43936ae87a46bff1d1
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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