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

HRID 615060Notes

Reaction equation

HRID 615060 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-0cdd54aa07a0416e8301c92df1140018
Source dataset
uspto-grants-1979_03
Patent number
US04146546

Reaction notes

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