Ethanethiol → HCID 9818633, compound

HRID 374025Notes

Reaction equation

HRID 374025 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(S)C.[CH3:8][N:9]([CH3:32])[CH2:10][CH2:11][N:12]1[C:28](=[O:29])[C:27]2[C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:30]C)[CH:24]=4)[NH:19][C:18]=3[CH:17]=[CH:16][C:15]=2[C:13]1=[O:14]>C(Cl)(Cl)Cl>[CH3:8][N:9]([CH3:32])[CH2:10][CH2:11][N:12]1[C:28](=[O:29])[C:27]2[C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([OH:30])[CH:24]=4)[NH:19][C:18]=3[CH:17]=[CH:16][C:15]=2[C:13]1=[O:14]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 19808758HCID 19808758, compound

Product 1

HCID 9818633HCID 9818633, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1.52 g of anhydrous aluminum chloride was suspended in 30 ml of chloroform. Thereto was added 1.69 ml of ethanethiol, and the mixture was stirred at room temperature for 10 minutes. Thereto was dropwise added, in 1 minute, a solution of 770 mg of N-(2-dimethylaminoethyl)-6-methoxycarbazole-3,4-dicarboximide dissolved in 100 ml of chloroform. The mixture was stirred at room temperature overnight. The solvent was removed by distillation under reduced pressure. The residue was mixed with 200 ml of ethyl acetate and 50 ml of an aqueous saturated sodium hydrogencarbonate solution. The mixture was stirred at room temperature for 30 minutes. The resulting insoluble material was removed by filtration. The separated insoluble material was washed with 50 ml of ethyl acetate. The washings were combined with the previously separated filtrate. 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 recrystallized from n-propanol to obtain 0.49 g (yield: 66%) of N-(2-dimethylaminoethyl)-6-hydroxycarbazole-3,4-dicarboximide as orange crystals.

Workup

  1. additionThereto was dropwise added, in 1 minute
  2. stirringThe mixture was stirred at room temperature overnight
  3. customThe solvent was removed by distillation under reduced pressure
  4. additionThe residue was mixed with 200 ml of ethyl acetate and 50 ml of an aqueous saturated sodium hydrogencarbonate solution
  5. stirringThe mixture was stirred at room temperature for 30 minutes
  6. customThe resulting insoluble material was removed by filtration
  7. washThe separated insoluble material was washed with 50 ml of ethyl acetate
  8. customThe organic layer was separated
  9. washwashed with an aqueous saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customThe residue was recrystallized from n-propanol

Sources & evidence

ORD record
ord-57bd9919e94246fc9bf9d963efd31fd2
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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