Ethanethiol → HCID 136401066, compound

HRID 1935591Notes

Reaction equation

HRID 1935591 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

Dimethylation 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-5b10030b90274c49a1a0bbe9f70a26b5
Source dataset
uspto-grants-2002_05
Patent number
US06387920B2

Reaction notes

Loading…