Hexamethylphosphoramide → 2,3-Dihydroxypropyl 4-(allylamino)phenylacetate

HRID 1278306Notes

Reaction equation

HRID 1278306 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[OH-].[Na+].I[CH2:18][CH:19]([OH:22])[CH2:20][OH:21].CN(C)P(N(C)C)(N(C)C)=O>O.CCOCC>[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:18][CH:19]([OH:22])[CH2:20][OH:21])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 38316Acetic acid, 2-(p-(allylamino)phenyl)-HCID 921273-Iodo-1,2-propanediol

Product 1

HCID 211634342,3-Dihydroxypropyl 4-(allylamino)phenylacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.34 g. of 4-(allylamino)phenylacetic 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-(allylamino)phenylacetate.

Workup

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

Sources & evidence

ORD record
ord-667b0a27861647229ccc9d50a57b931f
Source dataset
uspto-grants-1981_07
Patent number
US04281019

Reaction notes

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