Dimethylamine → N,N-dimethyl-4-(hexadecylamino)benzamide

HRID 2163758Notes

Reaction equation

HRID 2163758 reaction equation
C(Cl)Cl.S(Cl)(Cl)=O.Cl.[CH2:9]([NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[CH3:35][NH:36][CH3:37]>CN(C)C1C=CN=CC=1.C(COC)OC.C(OCC)C>[CH3:35][N:36]([CH3:37])[C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([NH:25][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 70506019HCID 70506019, compound

Product 1

HCID 20437361N,N-dimethyl-4-(hexadecylamino)benzamideYield 92%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

In a solution of 100 ml. of methylene dichloride and 25 ml. of glyme was dissolved in 10 ml. of thionyl chloride and 4.0 g. of 4-(n-hexadecylamino)benzoic acid hydrochloride. The reaction mixture was heated to the reflux temperature for 2 hours and then cooled to room temperature. To this solution of acid chloride was added a solution of 200 ml. of diethyl ether, 25 ml. of glyme, and 0.1 g. of 4-dimethylaminopyridine which had been saturated with dimethylamine gas. This reaction mixture was stirred at room temperature for 2 hours whereby there was obtained a 92% yield of product, melting point 70°-72° C.

Workup

  1. temperatureThe reaction mixture was heated to the reflux temperature for 2 hours

Sources & evidence

ORD record
ord-6ca705fce2b34ec2a96e2592a791f152
Source dataset
uspto-grants-1979_01
Patent number
US04136256

Reaction notes

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