Ethanethiol → HCID 1623, compound

HRID 1387073Notes

Reaction equation

HRID 1387073 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)[CH2:5][C:6]1[C:7]2[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][C:8]=2[S:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:13][CH:12]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[CH2:34][N:35]1[CH2:36][CH2:37][CH2:38][CH2:39]1)[CH2:5][C:6]1[C:7]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:8]=2[S:9][C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 10531733HCID 10531733, compound

Product 1

HCID 1623HCID 1623, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-[3-Bromo-4-[(1-pyrrolidinyl)methyl]benzyl]-6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (0.32 g; 0.53 mmol)(Part A) was dissolved in 9.0 mL of dichloroethane under an argon atmosphere and cooled in an ice-water bath. To this was added ethanethiol (0.78 mL; 10.56 mmol) and 0.70 g (5.28 mmol) of aluminum chloride, and the mixture was stirred in the cold bath for 1 h. Brine (80 mL) was added to the mixture, and stirring was continued while warming to room temperature for 1 h. Extraction was carried out with dichloromethane (4×75 mL). The combined organics were dried by passage through sodium sulfate. The title compound (0.23 g; 74% yield) was isolated as a white crystalline solid by flash chromatography on silica gel eluting with a gradient of EtOAc(100-85%)/Et3N(0-5%)/MeOH(0-10%).

Workup

  1. temperaturecooled in an ice-water bath
  2. stirringstirring
  3. extractionExtraction
  4. dry with materialThe combined organics were dried by passage through sodium sulfate

Sources & evidence

ORD record
ord-d0439abbff7d4296a01907f1fd912bf1
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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