Acetic Acid → HCID 54333419, compound

HRID 845320Notes

Reaction equation

[CH2:1]([C:5]1[C:6]([NH:8][C:9](=[O:11])[CH:10]=1)=[O:7])[CH2:2][CH2:3][CH3:4].C(O)(=O)C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[CH2:1]([C:5]1([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][C:9](=[O:11])[NH:8][C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 120 °C

Procedure

Maleic anhydride is reacted with n-butylamine under the conditions reported by L. E. Coleman et al., in J. Org. Chem., 24: 135, (1959). A mixture containing the thus-formed n-butylmaleamic acid (12.0 g, 0.07 mol), anhydrous sodium acetate (2.7 g) and acetic anhydride (29 mL) is heated at 85° C. to 90° C. for 30 minutes. The solution is cooled to 40° C. and poured into 55 mL of water. The layers are stirred at room temperature for 15 minutes, the diluted to 275 mL. A dark oil precipitates. Extraction with 100 mL of CH2Cl2, then another 25 mL of CH2Cl2, and evaporation of solvent gives 9.9 g of n-butylmaleimide as an oil, ir, 1735 (sh) and 1700 cm-1. A solution of 9.9 g (0.065 mol) of the n-butylmaleimide and 35 mL of acetic acid is treated with 6.51 g (0.07 mol) of aniline, with the resulting solution heated at 120° C. for 30 minutes. The solution is cooled and poured into 280 mL of water. The amorphous material is collected and recrystallized from isopropyl alcohol to give 9.3 g of n-butyl anilinosuccinimide as off-white crystals, m.p. 97°-100° C., ir, 3350, 1720 (sh), 1680, 1600 cm-1; mass spec, (ci) m/e 247. Anal. Calcd. for C14H18N202: C, 68.29; H, 7.32; N, 11.38. Found: C, 68.46; H, 7.28; N, 11.25.

Workup

temperatureThe solution is cooled
customThe amorphous material is collected
customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record: ord-bc1c5f3008d2497e8859591cab11a1ab
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04757146

Reaction notes

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