Hexamethylphosphoramide → 2,3-Dihydroxypropyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

HRID 2057661Notes

Reaction equation

HRID 2057661 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[OH-].[Na+].I[CH2:34][CH:35]([OH:38])[CH2:36][OH:37].CN(C)P(N(C)C)(N(C)C)=O>O.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([O:28][CH2:34][CH:35]([OH:38])[CH2:36][OH:37])=[O:27])=[CH:29][CH:30]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 921273-Iodo-1,2-propanediolHCID 203309694-[13-(4-Chlorophenyl)-12-tridecynylamino]benzoic acid

Product 1

HCID 203309552,3-Dihydroxypropyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.34 g. of 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoic acid, 4.80 g. of 25% aqueous sodium hydroxide, and 12.6 g. of 3-iodo-1,2-propanediol in 50 ml. of hexamethylphosphoramide is stirred for 24 hours at ambient temperature, diluted with 100 ml. of ether and stirred for 5 days at ambient temperature. The mixture is treated with water and extracted with ether. The dried extracts are evaporated to yield 2,3-dihydroxypropyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate.

Workup

  1. additiondiluted with 100 ml
  2. extractionextracted with ether
  3. customThe dried extracts are evaporated

Sources & evidence

ORD record
ord-5c238ea90a32469d861ef2f445d7ade1
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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