Hexamethylphosphoramide → 2,3-Dihydroxypropyl 4-(11-hydroxyundecylamino)benzoate

HRID 648313Notes

Reaction equation

HRID 648313 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1.[OH-].[Na+].I[CH2:26][CH:27]([OH:30])[CH2:28][OH:29].CN(C)P(N(C)C)(N(C)C)=O>O.CCOCC>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:20][CH2:26][CH:27]([OH:30])[CH2:28][OH:29])=[O:19])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 921273-Iodo-1,2-propanediolHCID 204825254-(11-Hydroxyundecylamino)benzoic acid

Product 1

HCID 204825382,3-Dihydroxypropyl 4-(11-hydroxyundecylamino)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.34 g. of 4-(11-hydroxyundecylamino)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-(11-hydroxyundecylamino)benzoate.

Workup

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

Sources & evidence

ORD record
ord-12e1e9adf95042da82d1d1d83cfa28af
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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