Dimethylformamide → Methyl N-methyl-5-nitro-N-[tris(hydroxymethyl)methyl]isophthalamate

HRID 1834173Notes

Reaction equation

COC([C:5]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:6]=1[C:7](Cl)=[O:8])=O.[CH3:17][NH:18][C:19]([CH2:24][OH:25])([CH2:22][OH:23])[CH2:20][OH:21].[C:26](=[O:29])([O-])[O-:27].[K+].[K+].[CH3:32]N(C)C=O>>[CH3:17][N:18]([C:19]([CH2:24][OH:25])([CH2:22][OH:23])[CH2:20][OH:21])[C:7](=[O:8])[C:6]1[CH:5]=[C:13]([CH:12]=[C:11]([N+:14]([O-:16])=[O:15])[CH:10]=1)[C:26]([O:27][CH3:32])=[O:29]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 10164823HCID 10164823, compound

HCID 13221842Methyl 2-(chlorocarbonyl)-4-nitrobenzoate

Product 1

HCID 22749370Methyl N-methyl-5-nitro-N-[tris(hydroxymethyl)methyl]isophthalamate

Procedure

Methoxy-carbonyl-5-nitrobenzoyl chloride [G. B. Hoey, et al., J. Med. Chem, 6, 24 (1963)] is added to a cold stirred slurry of N-methyl-tris(hydroxymethyl)-methylamine and potassium carbonate in dimethylformamide to form a solution of N-methyl-5-nitro-N-[tris(hydroxymethyl)methyl]isophthalamic acid, methyl ester.

Sources & evidence

ORD record: ord-216411be9e1a413dbd236d88c5546600
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04069250

Reaction notes

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