Dimethyl Sulfide → HCID 22568972, compound

HRID 395206Notes

Reaction equation

HRID 395206 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)=O)=[C:4]([CH3:14])[CH:3]=1.S(C)C.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:8][CH:9]2[CH2:10][CH2:11]2)=[C:4]([CH3:14])[CH:3]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 10340Sodium CarbonateHCID 225688404-bromo-N-cyclopropyl-2-methylbenzamide2×

Product 1

HCID 22568972HCID 22568972, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-bromo-N-cyclopropyl-2-methyl-benzamide (Intermediate 157, 1.81 g, 7.12 mmols) in THF (12 mL) was added BH3.SMe2 (1.08 g, 14.24 mmols). The solution was heated to 60° C. for 6 hours, cooled to room temperature and carefully treated with saturated aqueous Na2CO3 (30 mL) and stirred for 17 hours. This mixture was extracted with EtOAc and the combined organic layers were washed with H2O, saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound was isolated by column chromatography (10-15% EtOAc-hexanes).

Workup

  1. temperaturecooled to room temperature
  2. extractionThis mixture was extracted with EtOAc
  3. washthe combined organic layers were washed with H2O, saturated aqueous NaCl
  4. dry with materialbefore being dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50b880ef13484685a7518bd15a504678
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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