Dimethylamine → HCID 9804535, compound

HRID 864514Notes

Reaction equation

HRID 864514 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-55b7b368a03140bfae136ff27f223113
Source dataset
uspto-grants-1996_10
Patent number
US05563164

Reaction notes

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