Dimethylamine → HCID 9804535, compound

HRID 2260851Notes

Reaction equation

HRID 2260851 reaction equation
[CH2:1]([C:3]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:22]([OH:32])=[CH:21][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][C:18](O)=[O:19])[CH3:2].S(Cl)(Cl)=O.[CH3:37][NH:38][CH3:39]>ClCCl.O>[CH3:37][N:38]([CH3:39])[C:18](=[O:19])[CH2:17][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][CH2:8][CH2:7][CH2:6][O:5][C:4]1[CH:21]=[C:22]([OH:32])[C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:24][C:3]=1[CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 24386Thionyl ChlorideHCID 10160327HCID 10160327, compound

Product 1

HCID 9804535HCID 9804535, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-(3-(2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy)propoxy)phenyl)propionic acid and several equivalents of thionyl chloride in dichloromethane was kept at room temperature for 3 hours, and then poured into a stirred solution of 40% dimethylamine in water. The organic layer was washed with aqueous hydrochloric acid, washed with saturated sodium chloride, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate to provide the desired title product. NMR, MS.

Workup

  1. washThe organic layer was washed with aqueous hydrochloric acid
  2. washwashed with saturated sodium chloride
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-a0719742f6b448ddbf175250be0f2781
Source dataset
uspto-grants-1995_12
Patent number
US05478857

Reaction notes

Loading…