Methyl 4-Formylbenzoate → HCID 21101171, compound

HRID 1352655Notes

Reaction equation

HRID 1352655 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[CH:11]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)=O>[N+](C1C=CC=CC=1)([O-])=O.CCCCCC>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[N:9]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=3)[NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 792974,5-Dichloro-1,2-phenylenediamine

Product 1

HCID 21101171HCID 21101171, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 7416NitrobenzeneSolventHCID 8058HexaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4,5-dichlorophenylendiamine (4 g, 22.6 mmol) and methyl 4-formylbenzoate (3.68, 22.6 mmol) in nitrobenzene (35 ml) was heated at 140° C. for 30 h. After cooling, the mixture was diluted with n-hexane (150 ml) and stirred for 1 h. The solid was filtered obtaining 5 g of the title compound (yield 68.9%) as a brown powder, mp=240–250° C.

Workup

  1. temperatureAfter cooling
  2. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-66b44b69be36455fb0d68af7a91543ae
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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