Water → 2,3-Dihydroxypropyl 2-fluoro-4-(hexadecylamino)benzoate

HRID 1156113Notes

Reaction equation

HRID 1156113 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].I[CH2:31][CH:32]([OH:35])[CH2:33][OH:34].O>CN(C)P(N(C)C)(N(C)C)=O.CCOCC>[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:31][CH:32]([OH:35])[CH2:33][OH:34])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 921273-Iodo-1,2-propanediolHCID 205364112-Fluoro-4-(hexadecylamino)benzoic acid

Product 1

HCID 205365042,3-Dihydroxypropyl 2-fluoro-4-(hexadecylamino)benzoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 7.34 g. of 2-fluoro-4-(hexadecylamino)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 2-fluoro-4-(hexadecylamino)benzoate.

Workup

  1. extractionextracted with ether
  2. customThe dried extracts are evaporated

Sources & evidence

ORD record
ord-6299707ec6524895b0447a8da4f7973f
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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