Ethanethiol → HCID 136401066, compound

HRID 351911Notes

Reaction equation

HRID 351911 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][NH:24]4)=[CH:16][CH:15]=3)=[C:12]([C:29]3[CH:34]=[CH:33][C:32]([O:35]C)=[CH:31][CH:30]=3)[O:11][N:10]=2)=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(S)C>ClC(Cl)C>[OH:35][C:32]1[CH:33]=[CH:34][C:29]([C:12]2[O:11][N:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=3)[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][NH:24]3)=[CH:16][CH:15]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 69545726HCID 69545726, compound

Product 1

HCID 136401066HCID 136401066, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Demethylation was performed using Method 2 described for Step C in Scheme I. To a solution of the isoxazole obtained from step 6 (1.0 equiv.) in dichloroethane was added aluminum chloride (5.0 equiv.) and ethane thiol (5.0 equiv.). The resultant mixture was stirred for 40 min at room temperature and quenched with THF, 20% HCl and water. A precipitate was formed and this was collected by filtration. After drying the product the material was taken up in methanol, treated with activated charcoal, filtered through sodium sulfate and concentrated in vacuo. Purification with flash chromatography followed by addition of HCl aq. and lyophilization, then afforded the product 4-{5-(4-hydroxyphenyl)-4-[4-(2-piperidylethoxy)phenyl]isoxazol-3-yl}phenol as hydrochloride salt.

Workup

  1. customquenched with THF, 20% HCl and water
  2. customA precipitate was formed
  3. filtrationthis was collected by filtration
  4. customAfter drying the product the material
  5. additiontreated with activated charcoal
  6. filtrationfiltered through sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification with flash chromatography
  9. additionfollowed by addition of HCl aq. and lyophilization

Sources & evidence

ORD record
ord-fe49ea08f1c446b084831cc46d99a19c
Source dataset
uspto-grants-2004_06
Patent number
US06743815B2

Reaction notes

Loading…