Glutaric anhydride → HCID 53757038, compound

HRID 1065808Notes

Reaction equation

HRID 1065808 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 1140TolueneSolvent2×

Procedure

A stirred solution of 0.83 g. of the N-(1-methyldecyl)-3-(3-aminophenyl)-2-butenamide from Preparation 28 in 25 ml. of toluene was heated on a steam bath, and 0.31 g. of glutaric anhydride was added in one portion. After 5 minutes, the solution was concentrated in vacuo, which caused a gum to form. The remaining toluene was poured off, and the residue was induced to solidify by trituration under petroleum ether. The solid was recrystallized three times from acetonitrile, giving 261 mg. of the title compound, m.p. 115°-117.5° C. The IR spectrum (KBr disc) showed absorptions at 3279, 2941, 1709, 1667, 1639, 1600 and 1550 cm-1. The NMR spectrum (DMSO-d6) showed absorptions at 0.82 (m, 3H), 0.94 (m, 3H), 1.21 (s, 16H), 1.85 (m, 2H), 2.05 (m, 3H), 2.32 (m, 4H, under DMSO-d6), 3.60 (m, 1H), 5.89 (d, 1H), 7.20 (m, 6H) and 9.80 (s, 1H) ppm.

Workup

  1. concentrationthe solution was concentrated in vacuo, which
  2. customto form
  3. customThe solid was recrystallized three times from acetonitrile
  4. customgiving 261 mg

Sources & evidence

ORD record
ord-8da06c068bf44bee8831dbed9b988463
Source dataset
uspto-grants-1982_05
Patent number
US04331683

Reaction notes

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