Ethanol → HCID 13561922, compound
Reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH:3]([C:14]([OH:16])=[O:15])[NH:2]1.[OH-].[K+].[CH2:19](O)[CH3:20].C(I)C.[C:25](=[S:27])=[S:26]>>[CH2:19]([S:27][C:25]([N:2]1[CH:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1]1)=[S:26])[CH3:20]Participants
Procedure
To a mixture of (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (4.32 g), KOH (96%, 2.34 g) and 50% ethanol (80 ml) is added dropwise carbon disulfide (1.8 ml) at room temperature, and the mixture is stirred at the same temperature for 30 minutes. To the mixture is added dropwise ethyl iodide (4.68 g), and the mixture is further stirred at room temperature for 48 hours and distilled to remove the solvent. To the residue is added water, and the mixture is washed with ether. The aqueous layer is acidified with 10% HCl and extracted with ethyl acetate. The extract is washed with water, dried and then distilled to remove the solvent. The residue is recrystallized from chloroform to give the title compound (4.45 g, 69%) as colorless needles, m.p. 177°-178° C., NMR (CDCl3 --DMSO--d6, δ): 1.38 (t, J=7.0 Hz, 3H, N--CSSCH2CH3), 3.34 (q, J=7.0 Hz, 2H, N--CSSCH2CH3), Mass (m/e): 320 (M+), 258 (M+ --CH3CH2SH)
Workup
- stirringthe mixture is further stirred at room temperature for 48 hours
- distillationdistilled
- customto remove the solvent
- additionTo the residue is added water
- washthe mixture is washed with ether
- extractionextracted with ethyl acetate
- washThe extract is washed with water
- customdried
- distillationdistilled
- customto remove the solvent
- customThe residue is recrystallized from chloroform
Sources & evidence
- ORD record
- ord-3330957d451640a7b0de2c14e736fb6e
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04628057
Reaction notes
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