Water → 4-(dodecanoylamino)benzoic acid

HRID 847680Notes

Reaction equation

HRID 847680 reaction equation
[C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1.O>N1C=CC=CC=1>[C:1]([NH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 9784-Aminobenzoic AcidHCID 8166Dodecanoyl chloride

Product 1

HCID 46949794-(dodecanoylamino)benzoic acidYield 86.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

n-Dodecanoyl chloride (8.74 g; 40 mmoles) is added dropwise to a solution of p-aminobenzoic acid (5.5 g; 40 mmoles) dissolved in pyridine (100 ml). The mixture is stirred for 3 hours and poured into water (3 L). The precipitate which forms is filtered and dried in vacuo to give N-(n-dodecanoyl)-p-aminobenzoic acid (11.01 g).

Workup

  1. filtrationThe precipitate which forms is filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-91ea9e30b3b74fd0a8df91a40e7d9ef6
Source dataset
uspto-grants-1981_10
Patent number
US04293482

Reaction notes

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