Water → HCID 3101360, compound

HRID 2254516Notes

Reaction equation

HRID 2254516 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].[N+:12]([C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[C:18](Cl)=[O:19])([O-:14])=[O:13].O>C(#N)C.CC(N(C)C)=O.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH:5][C:18](=[O:19])[C:17]1[CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=1

Participants

7

Reactant 3

HCID 962WaterHCID 74323,5-Dinitrobenzoyl chlorideHCID 76132,5-Dimethoxyaniline

Product 1

HCID 3101360HCID 3101360, compoundYield 106.2%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

In 2 l of acetonitrile, 1.2 l of dimethylacetamide and 0.186 l of pyridine was dissolved 306.4 g of 2,5-dimethoxyaniline. While cooling the resulting solution with ice, 507.8 g of 3,5-dinitrobenzoyl chloride was slowly added thereto. While keeping the temperature of the reaction mixture at 15° C., the mixture was stirred for 3 hours and poured into 600 ml of water. The precipitated crystal was recovered by filtration, washed with acetonitrile and dried to obtain 737.5 g of the compound (7-A). Yield: 99%.

Workup

  1. additionwas slowly added
  2. customat 15° C.
  3. filtrationThe precipitated crystal was recovered by filtration
  4. washwashed with acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-74bbe5f53e8e4b6dba536fe3d9587f6a
Source dataset
uspto-grants-1993_08
Patent number
US05236803

Reaction notes

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