2-Propanethiol → HCID 18963787, compound

HRID 2226862Notes

Reaction equation

HRID 2226862 reaction equation
Br[C:2]1[C:3]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH3:16][CH:17]([SH:19])[CH3:18].N12CCCN=C1CCCCC2>CN(C)C=O>[Cl:15][C:14]1[C:3]2[C:2]([S:19][CH:17]([CH3:18])[CH3:16])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[S:5][C:4]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18963779HCID 18963779, compound

Product 1

HCID 18963787HCID 18963787, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 3-bromo-4-chlorobenzo[b]thiophene-2-carboxylate (0.62 g, 2.0 mmol) , 2-propanethiol (0.30 mL, 0.25 g, 3.2 mmol) , and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.33 mL, 0.34 g, 2.2 mmol) in 5.0 mL of N,N-dimethylformamide is stirred at room temperature for 24 hours. The reaction mixture is partitioned between 150 mL of cold 1.0N HCl and 75 mL of dichloromethane, and the aqueous layer is extracted several times with fresh dichloromethane. The combined organic layers are washed with 1.0N HCl and brine, then dried (anhydrous sodium sulfate) and evaporated to yield methyl 4-chloro-3-[(1-methylethyl)thio]benzo[b]thiophene-2-carboxylate as an oil.

Workup

  1. customThe reaction mixture is partitioned between 150 mL of cold 1.0N HCl and 75 mL of dichloromethane
  2. extractionthe aqueous layer is extracted several times with fresh dichloromethane
  3. washThe combined organic layers are washed with 1.0N HCl and brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-fdf3757da4cc4b2ba76b181d24ae6107
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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