Dimethylacetamide → beta-Alanine, N-(3-acetamido-5-methylcarbamoyl-2,4,6-triiodobenzoyl)-

HRID 1606669Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[C:6]([I:22])=[C:7]([C:16]([I:21])=[C:17]([NH2:20])[C:18]=1[I:19])[C:8]([NH:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:9])=[O:4].[CH3:23][C:24](N(C)C)=[O:25]>>[CH3:1][NH:2][C:3]([C:5]1[C:6]([I:22])=[C:7]([C:16]([I:21])=[C:17]([NH:20][C:24](=[O:25])[CH3:23])[C:18]=1[I:19])[C:8]([NH:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:9])=[O:4]

Participants

Reactant 2

HCID 31374Dimethylacetamide

HCID 54065167HCID 54065167, compound

Product 1

HCID 39523beta-Alanine, N-(3-acetamido-5-methylcarbamoyl-2,4,6-triiodobenzoyl)-Yield 66%

Procedure

From 100.0 g. (0.155 mole) of N-(3-methylaminocarbonyl-5-amino-2,4,6-triiodobenzoyl)-β-alanine (IX c), m.p. about 190° C., in 190 ml. of dimethylacetamide, 70.1 g. (66.0%) of the above product, m.p. 295°-297°C. (under decomposition) is obtained with the addition of 28.7 ml. of acetyl chloride analogously to Example 14 and after reprecipitation from aqueous ammonia with hydrochloric acid.

Sources & evidence

ORD record: ord-64ed42c530184792a31c9eefd758e447
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03953501

Reaction notes

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