Ethanethiol → HCID 21182697, compound

HRID 1387070Notes

Reaction equation

HRID 1387070 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[C:15]([Br:25])[CH:14]=3)=[O:12])=[C:9]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:28][CH:27]=3)[S:8][C:7]=2[CH:40]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[C:15]([Br:25])[CH:14]=3)=[O:12])=[C:9]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:28][CH:27]=3)[S:8][C:7]=2[CH:40]=1

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 10746430HCID 10746430, compound

Product 1

HCID 21182697HCID 21182697, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4-[3-Bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone (34 mg; 0.055 mmol) (Part D) was dissolved in dichloroethane (5 mL) in a flame-dried, argon-filled flask, and cooled in an ice-water bath. Ethanethiol (0.16 mL; 2.2 mmol) was added, followed by 0.15 g (1.1 mmol) of aluminum chloride. The resultant slurry was stirred in the cold for 2 h. Saturated aqueous sodium bicarbonate (20 mL) was added, and stirring was continued for 2 h. Extraction was carried out with EtOAc (4×25 mL) and the combined organics were washed with brine and dried by passage through sodium sulfate. The product was isolated as a yellow oil (19 mg; 57% yield) by flash chromatography on silica gel, eluting with a gradient of EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%).

Workup

  1. additionfilled flask
  2. temperaturecooled in an ice-water bath
  3. stirringstirring
  4. waitwas continued for 2 h
  5. extractionExtraction
  6. washthe combined organics were washed with brine
  7. dry with materialdried by passage through sodium sulfate
  8. customThe product was isolated as a yellow oil (19 mg; 57% yield) by flash chromatography on silica gel
  9. washeluting with a gradient of EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%)

Sources & evidence

ORD record
ord-e694206fd4d540e4bd91676235ffe057
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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