Ethanethiol → HCID 18397552, compound

HRID 1387003Notes

Reaction equation

HRID 1387003 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C@@H:19]4[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]4[N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:14][CH:13]=3)=[C:9]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][N:40]4[CH2:44][CH2:43][CH2:42][CH2:41]4)=[CH:33][CH:32]=3)[S:8][C:7]=2[CH:45]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C@@H:19]4[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]4[N:25]4[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]4)=[CH:14][CH:13]=3)=[C:9]([C:31]3[CH:32]=[CH:33][C:34]([O:37][CH2:38][CH2:39][N:40]4[CH2:41][CH2:42][CH2:43][CH2:44]4)=[CH:35][CH:36]=3)[S:8][C:7]=2[CH:45]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 18397564HCID 18397564, compound

Product 1

HCID 18397552HCID 18397552, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1.150 g (1.84 mmol) (±)-6-methoxy-3-[4-[[trans-2-(1-piperidyl)cyclohexyl]oxy]benzyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (Part A) in 20.0 mL of anhydrous dichloroethane at 0° C. was added 1.10 mL (14.7 mmol) of ethanethiol, followed by the addition of aluminum chloride (982 mg, 7.36 mmol). The yellow biphasic reaction mixture was allowed to warm to room temperature and stirred for 3 h. The reaction was quenched at 0° C. with 20 mL of saturated aqueous NaHCO3. The aqueous layer was separated and extracted with EtOAc (3×200 mL). The combined organic layers were washed with 150 mL of brine, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified by using flash chromatography (silica gel, 60:37:3 THF-hexanes-TEA) to afford 1.067 g (1.75 mmol, 95%) of a white solid.

Workup

  1. customThe yellow biphasic reaction mixture
  2. customThe reaction was quenched at 0° C. with 20 mL of saturated aqueous NaHCO3
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc (3×200 mL)
  5. washThe combined organic layers were washed with 150 mL of brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-9840ff8b47f8477ea275ef1b062e866f
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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