Hydrochloric Acid → HCID 12797215, compound

HRID 2412590Notes

Reaction equation

HRID 2412590 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].C(N(CC)CC)C.[C:19](Cl)(=[O:35])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].Cl>CN(C)C=O.O>[C:19]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6])(=[O:35])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 755683-Amino-4-methylbenzoic acid

Product 1

HCID 12797215HCID 12797215, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 3-amino-4-methylbenzoic acid (15.1 g) in dry dimethylformamide (150 ml), containing triethylamine (20.2 g) was treated with n-hexadecanoyl chloride (27.5 g) during 30 minutes. The temperature of the reaction mixture was maintained at 25°-45° C. during the addition by water cooling. The mixture was then stirred for a further hour and was poured into water (1000 ml). The mixture was adjusted to pH 1 by the addition of concentrated hydrochloric acid (strength 0.6% w.v). The solid was collected, was washed with water and was recrystallised from ethanol (1500 ml) to give 3-(n-hexadecanamido)-4-methylbenzoic acid (22.0 g), in the form of a white solid, m.p. 238°-240° C.

Workup

  1. customThe solid was collected
  2. washwas washed with water
  3. customwas recrystallised from ethanol (1500 ml)

Sources & evidence

ORD record
ord-4a13b4c97de64034986eb21ffaf3cb82
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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