Glutaric anhydride → HCID 53757038, compound

HRID 1065807Notes

Reaction equation

HRID 1065807 reaction equation
[CH3:1][CH:2]([NH:12][C:13](=[O:24])[CH:14]=[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1)[CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:25]1(=[O:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[CH3:1][CH:2]([NH:12][C:13](=[O:24])[CH:14]=[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:25](=[O:32])[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH:18]=1)[CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 54502184HCID 54502184, compound

Product 1

HCID 53757038HCID 53757038, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 0.61 g. of N-(1-methyldecyl)-3-(3-aminophenyl)-2-butenamide, prepared in a manner analogous to Preparation 27, in 25 ml. of toluene, was heated on a steam bath and then 0.23 g. of glutaric anhydride was added in one portion. After 5 minutes, the reaction mixture was cooled and the solvent was removed by evaporation in vacuo. The residue was recrystallized twice from acetonitrile, to give 370 mg. of the title compound, m.p. 136°-140° C. This latter material was recrystallized from isopropanol/water to give 196 mg. of material having a melting point of 140°-141.5° C. The IR spectrum (KBr disc) showed absorptions at 3390, 2895, 1724, 1681, 1613 and 1575 cm-1. The NMR spectrum (DMSO-d6) showed absorptions at 0.90 (m, 3H), 1.08 (m, 3H), 1.26 (s, 16H), 1.89 (m, 2H), 2.40 (m, 7H, under DMSO-d6), 3.80 (m, 1H), 6.19 (s, 1H), 7.51 (m, 6H), and 9.90 (s, 1H) ppm.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customthe solvent was removed by evaporation in vacuo
  3. customThe residue was recrystallized twice from acetonitrile
  4. customto give 370 mg

Sources & evidence

ORD record
ord-8706166a3716471691bd2bb9b9c63d0d
Source dataset
uspto-grants-1982_05
Patent number
US04331683

Reaction notes

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