Hexamethylphosphoramide → 2,3-Dihydroxypropyl 4-(8-cyclohexyloctylamino)benzoate

HRID 905276Notes

Reaction equation

HRID 905276 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].I[CH2:28][CH:29]([OH:32])[CH2:30][OH:31].CN(C)P(N(C)C)(N(C)C)=O>O.CCOCC>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O:22][CH2:28][CH:29]([OH:32])[CH2:30][OH:31])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 921273-Iodo-1,2-propanediolHCID 204757724-(8-Cyclohexyloctylamino)benzoic acid

Product 1

HCID 204758122,3-Dihydroxypropyl 4-(8-cyclohexyloctylamino)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.34 g. of 4-(8-cyclohexyloctylamino)-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 the product.

Workup

  1. additiondiluted with 100 ml
  2. extractionextracted with ether
  3. customThe dried extracts are evaporated
  4. customto yield the product

Sources & evidence

ORD record
ord-9d7ed929fa694e7ab5dbde21e98df3f4
Source dataset
uspto-grants-1983_12
Patent number
US04423051

Reaction notes

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