Hydrochloric Acid → p-(15-Carbomethoxypentadecylamino)benzoic acid

HRID 1278395Notes

Reaction equation

HRID 1278395 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28].C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C)P(N(C)C)(N(C)C)=O>[C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)([O:29][CH3:30])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 10340Sodium CarbonateHCID 2736822Methyl 16-bromohexadecanoate

Product 1

HCID 12898273p-(15-Carbomethoxypentadecylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 1.37 g. of 4-aminobenzoic acid, 3.50 g. of methyl 16-bromohexadecanoate, 2.12 g. of sodium carbonate and 140 ml. of hexamethylphosphoramide is stirred at 120° C. for 18 hours, allowed to cool, and poured into dilute hydrochloric acid. The precipitate is collected by filtration, dried, and crystallized from acetonitrile to yield 4-(15-carbomethoxypentadecylamino)benzoic acid as a white solid.

Workup

  1. additionA mixture of 1.37 g
  2. temperatureto cool
  3. filtrationThe precipitate is collected by filtration
  4. customdried
  5. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-01f9acbf1ac14c66898d011b1308e1fe
Source dataset
uspto-grants-1981_07
Patent number
US04281018

Reaction notes

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