Hydrogen Bromide → 4-(16-Bromohexadecylamino)benzoic acid

HRID 648325Notes

Reaction equation

HRID 648325 reaction equation
O[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][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1.[BrH:28].S(=O)(=O)(O)O>C(O)(=O)C>[Br:28][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][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 204825164-(16-Hydroxyhexadecylamino)benzoic acid

Product 1

HCID 204825194-(16-Bromohexadecylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 16 g. of 4-(16-hydroxyhexadecylamino)benzoic acid and 150 g. of 30-32% hydrogen bromide in acetic acid is treated with 30 ml. of concentrated sulfuric acid, stirred under reflux for 8 hours, poured into ice-water, and filtered. The product is washed with water, dried and recrystallized from ether-petroleum ether to yield 4-(16-bromohexadecylamino)benzoic acid as a white, crystalline solid.

Workup

  1. additionA mixture of 16 g
  2. temperatureunder reflux for 8 hours
  3. filtrationfiltered
  4. washThe product is washed with water
  5. customdried
  6. customrecrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-e8ef99abb7ac4410ba429cf1a4d93b54
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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