Ethanethiol → HCID 19808735, compound

HRID 374035Notes

Reaction equation

HRID 374035 reaction equation
C(S)C.[CH2:4]([N:6]([CH2:37][CH3:38])[CH2:7][CH2:8][N:9]1[C:25](=[O:26])[C:24]2[C:23]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:27]CC5C=CC=CC=5)[CH:21]=4)[NH:16][C:15]=3[C:14]([O:35][CH3:36])=[CH:13][C:12]=2[C:10]1=[O:11])[CH3:5].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:37]([N:6]([CH2:4][CH3:5])[CH2:7][CH2:8][N:9]1[C:25](=[O:26])[C:24]2[C:23]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([OH:27])[CH:21]=4)[NH:16][C:15]=3[C:14]([O:35][CH3:36])=[CH:13][C:12]=2[C:10]1=[O:11])[CH3:38]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 516892Sodium BicarbonateHCID 19808721HCID 19808721, compound

Product 1

HCID 19808735HCID 19808735, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.8 ml of ethanethiol and 0.47 ml of boron trifluoride-diethyl ether complex were added to 180 mg of N-(2-diethylaminoethyl)-6-benzyloxy-1-methoxycarbazole-3,4-dicarboximide. The mixture was stirred at room temperature overnight. Thereto were added 100 ml of ethyl acetate and 50 ml of an aqueous saturated sodium hydrogencarbonate solution. The mixture was stirred at room temperature for 10 minutes. The organic layer was separated 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 10/1), followed by recrystallization from ethanol to obtain 26 mg (yield: 18%) of N-(2-diethylaminoethyl)-6-hydroxy- 1-methoxycarbazole-3,4-dicarboximide as yellow crystals.

Workup

  1. stirringThe mixture was stirred at room temperature for 10 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography (eluant: chloroform/methanol=40/1 to 10/1)
  6. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-d3da1354150c44198348b3d937024725
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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