Dimethylformamide → HCID 14054009, compound

HRID 846812Notes

Reaction equation

HRID 846812 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([NH:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1C(O)=O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](Cl)(=[O:27])C(Cl)=O.CN(C)C=O.[N+:34]([C:37]1[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=1[NH2:39])([O-:36])=[O:35]>C(OCC)(=O)C.N1C=CC=CC=1>[N+:34]([C:37]1[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=1[NH:39][C:23](=[O:27])[C:20]1[CH:19]=[CH:15][C:14]([NH:13][C:11](=[O:12])[CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:22][CH:21]=1)([O-:36])=[O:35]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 69462-NitroanilineHCID 65578Oxalyl chlorideHCID 54356780HCID 54356780, compound

Product 1

HCID 14054009HCID 14054009, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(2'-Nitrophenyl)-4-(3-benzyloxypropanoylamino)-benzamide is prepared analogously to Example 1 using 12 g (40.1 mMole) 4 (3 benzyloxypropanoylamino)-benzoic acid, 6.6 g (0.13 mMole) oxalyl chloride, 9.7 g (0.13 mole) dimethylformamide, 2×4.5 g pyridine, 6.1 g (44.1 mMole) o-nitroaniline, and 280 mL dry ethyl acetate. The crude product is purified by column chromatography (silica gel; ethyl acetate/n hexane 1:5-1:1 v/v). Yield 3.5 g (21% of theory); m.p. 140° C.

Workup

  1. customThe crude product is purified by column chromatography (silica gel; ethyl acetate/n hexane 1:5-1:1 v/v)

Sources & evidence

ORD record
ord-69aa677fe66f4e5d8f1769857a78de70
Source dataset
uspto-grants-1992_08
Patent number
US05137918

Reaction notes

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