Dimethylformamide → HCID 18626199, compound

HRID 1859654Notes

Reaction equation

HRID 1859654 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[N+:18]([O-])=O.CN(C=O)C.[Cl:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][C:33]=1[CH3:34])[NH2:30]>ClCCl.CO>[NH2:18][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:9]=1[O:8][CH3:7])[C:13]([NH:30][C:29]1[CH:31]=[CH:32][C:33]([CH3:34])=[C:27]([Cl:26])[CH:28]=1)=[O:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72553-Chloro-4-methylanilineHCID 65578Oxalyl chlorideHCID 666404-Methoxy-3-nitrobenzoic acid

Product 1

HCID 18626199HCID 18626199, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared according to the procedure described for Example 1 using oxalyl chloride (3.0 mL, 4.39 mmol), 4-methoxy-3-nitrobenzoic acid (5.00 g, 25.36 mmol), DMF (1.0 mL, 12.92 mmol), and 3-chloro-4-methylaniline (7.0 mL, 57.69 mmol). Chromatography on silica gel in 95:5 dichloromethane/methanol gave the product, (2.72 g), m.p. 153-157° C.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-bcf19f9ede7944b3bef80bd4de92bd33
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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