Ethanethiol → HCID 19808720, compound

HRID 374037Notes

Reaction equation

HRID 374037 reaction equation
[H-].[Na+].C(S)C.[CH3:6][N:7]([CH3:33])[CH2:8][CH2:9][N:10]1[C:26](=[O:27])[C:25]2[C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([O:28]C)[CH:22]=4)[NH:17][C:16]=3[C:15]([CH2:30][O:31][CH3:32])=[CH:14][C:13]=2[C:11]1=[O:12]>CN(C)C=O>[CH3:6][N:7]([CH3:33])[CH2:8][CH2:9][N:10]1[C:26](=[O:27])[C:25]2[C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([OH:28])[CH:22]=4)[NH:17][C:16]=3[C:15]([CH2:30][O:31][CH3:32])=[CH:14][C:13]=2[C:11]1=[O:12]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 19808749HCID 19808749, compound

Product 1

HCID 19808720HCID 19808720, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

520 mg of 60% sodium hydride was suspended in 10 ml of N,N-dimethylformamide. Thereto was dropwise added a solution of 0.87 ml of ethanethiol dissolved in 5 ml of N,N-dimethylformamide, in 5 minutes with stirring at room temperature. Then, thereto was added 90 mg of N-(2-dimethylaminoethyl)-6-methoxy-1-methoxymethylcarbazole-3,4-dicarboximide. The mixture was stirred at room temperature overnight. The solvent was removed by distillation under reduced pressure. The residue was mixed with 50 ml of ethyl acetate and 20 ml of water. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: chloroform/methanol=40/1 to 20/1), followed by recrystallization from n-propanol to obtain 30 mg (yield: 35%) of N-(2-dimethylaminoethyl)-6-hydroxy-1-methoxymethylcarbazole-3,4-dicarboximide as yellow crystals.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe solvent was removed by distillation under reduced pressure
  3. additionThe residue was mixed with 50 ml of ethyl acetate and 20 ml of water
  4. customThe organic layer was separated
  5. washwashed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by column chromatography (eluant: chloroform/methanol=40/1 to 20/1)
  9. customfollowed by recrystallization from n-propanol

Sources & evidence

ORD record
ord-61a62eb4ccce4a70ad4eaa9681d1aac4
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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