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

HRID 903415Notes

Reaction equation

HRID 903415 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-4743a01f29bd4b1eb6f9dc921ea294ed
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

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