Sodium methanethiolate → HCID 18449360, compound

HRID 1921189Notes

Reaction equation

HRID 1921189 reaction equation
Br[C:2]1[N:3]=[C:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[S:5][CH:6]=1.[CH3:17][S-:18].[Na+]>CN(C=O)C.[Cu](I)I>[CH3:17][S:18][C:2]1[N:3]=[C:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[S:5][CH:6]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolate2×HCID 18449359HCID 18449359, compound

Product 1

HCID 18449360HCID 18449360, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1-(4-bromo-1,3-thiazol-2-yl)-1,3-dihydro-2H-benzimidazol-2-one from Step A (1.00 g, 3.38 mmol), sodium methanethiolate (710 mg, 10.13 mmol), and copper iodide (643 mg, 3.38 mmol) in DMF (6 mL) were heated at 140° C. An additional amount of sodium methanethiolate (474 mg, 6.76 mmol) was added to the mixture after 3 h and 16 h and the reaction continued stirring at 140° C. After 20 h, the cooled mixture was partitioned between saturated aqueous NaHCO3 (30 mL) and CHCl3 (50 mL). The aqueous phase was extracted further with CHCl3 (50 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to give the title compound. MS: m/z=264 (M+1).

Workup

  1. customthe cooled mixture was partitioned between saturated aqueous NaHCO3 (30 mL) and CHCl3 (50 mL)
  2. extractionThe aqueous phase was extracted further with CHCl3 (50 mL)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29d6bb6ed0aa4340ba74ec1aac25fd33
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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