Acetic Anhydride → HCID 21880474, compound

HRID 845319Notes

Reaction equation

C1(=O)OC(=O)C=C1.C(N)CCC.[CH2:13](/[C:17](=[CH:21]/[C:22]([NH2:24])=[O:23])/[C:18](O)=[O:19])[CH2:14][CH2:15][CH3:16].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O>[CH2:13]([C:17]1[C:18]([NH:24][C:22](=[O:23])[CH:21]=1)=[O:19])[CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 40 °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

temperatureis heated at 85° C. to 90° C. for 30 minutes
additionthe diluted to 275 mL
customA dark oil precipitates
extractionExtraction with 100 mL of CH2Cl2
customanother 25 mL of CH2Cl2, and evaporation of solvent

Sources & evidence

ORD record: ord-fc5b21bd22bf49b39ac04ab4d6d1232f
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04757146

Reaction notes

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