Water → 2-phthalimido-N-(1,1-dimethylhexyl)acetamide

HRID 1277477Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

2-Methylheptan-2-ol (56.53 g.; 0.43 mole) and phthalimidoacetonitrile (80.27 g.; 0.43 mole) were dissolved in glacial acetic acid (220 ml.) and the solution warmed to about 60° C. with stirring. Concentrated sulphuric acid (59 ml.; 1.1 mole) was then added gradually; at first the temperature fell but as the addition proceeded a vigorous exothermal reaction took place, the temperature of the reaction was controlled at 70° C. by regulating the addition of the sulphuric acid and coolingas necessary. When the addition was complete the resulting dark brown solution was stirred for 11/2 hours and then added dropwise to a mixture of ice and water. The precipitated solid was filtered off, pressed well, washed with fresh water and dried in vacuo. The residue was recrystallisedfrom benzene with filtering, to afford 2-phthalimido-N-(1,1-dimethylhexyl)acetamide m.p. 142° C.

Workup

additionat first the temperature fell but as the addition
customa vigorous exothermal reaction
customwas controlled at 70° C.
additionWhen the addition
stirringwas stirred for 11/2 hours
filtrationThe precipitated solid was filtered off
washwashed with fresh water
customdried in vacuo
filtrationwith filtering

Sources & evidence

ORD record: ord-39a020b28c4249eabfc76373e49878a0
Source dataset: uspto-grants-1981_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04277498

Reaction notes

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