Water → 2-phthalimido-N-(1,1,5-trimethylhexyl)acetamide

HRID 1277485

Reaction equation

[C:1]1(=[O:14])[N:5]([CH2:6][C:7]#[N:8])[C:4](=[O:9])[C:3]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:2]12.[CH3:15][C:16](O)([CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH3:17].S(=O)(=O)(O)[OH:26].O>C(O)(=O)C>[C:4]1(=[O:9])[N:5]([CH2:6][C:7]([NH:8][C:16]([CH3:17])([CH3:15])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:26])[C:1](=[O:14])[C:2]2=[CH:13][CH:12]=[CH:11][CH:10]=[C:3]12

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of phthalimidoacetonitrile (6.01 g, 0.03 mole) in glacial acetic acid (16 ml) was heated to 60° C. with stirring; 2,6-dimethylheptan-2-ol (4.64 g, 0.03 mole) was then added followed dropwise by concentrated sulphuric acid (4.4 ml, 0.08 mole). The temperature rapidly rose to 20° and was controlled at this temperature during the addition. When the addition was complete the solution was stirred for 5 minutes and then added slowly to a mixture of ice and water (350 g). The precipitated solid was filtered off, washed thoroughly with water and dried in vacuo. The product was recrystallised from benzene with filtering to afford 2-phthalimido-N-(1,1,5-trimethylhexyl)acetamide, m.p. 162°-163°.

Workup

customrapidly rose to 20°
additionwas controlled at this temperature during the addition
additionWhen the addition
stirringwas stirred for 5 minutes
filtrationThe precipitated solid was filtered off
washwashed thoroughly with water
customdried in vacuo
customThe product was recrystallised from benzene
filtrationwith filtering

Sources & evidence

ORD record: ord-a48c9c223f89431c8439d70714812a71
Source dataset: uspto-grants-1981_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04277498

Linked notes

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