Allyl bromide → 2-Propenyl 4-(n-hexadecylamino)benzoate

HRID 1439302Notes

Reaction equation

HRID 1439302 reaction equation
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([O-:24])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Na+].[CH2:28](Br)[CH:29]=[CH2:30]>CN(C)P(N(C)C)(N(C)C)=O>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:30][CH:29]=[CH2:28])=[O:23])=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 23703815Cetaben Sodium

Product 1

HCID 132553192-Propenyl 4-(n-hexadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 7.66 g. of sodium 4-(n-hexadecylamino)benzoate and 12.1 g. of allyl bromide in 100 ml. of dry hexamethylphosphoramide is added to a reaction flask. After 6 hours the solution is poured into 100 ml. of water and the solid collected and recrystallized from 50 ml. of acetonitrile. This material is recrystallized from hexanol to yield the title compound, m.p. 81°-83° C.

Workup

  1. additionAfter 6 hours the solution is poured into 100 ml
  2. customof water and the solid collected
  3. customrecrystallized from 50 ml
  4. customThis material is recrystallized from hexanol

Sources & evidence

ORD record
ord-9b87f412f103432081adfd728f0973fe
Source dataset
uspto-grants-1977_11
Patent number
US04058550

Reaction notes

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