Hydrochloric Acid → (3RS)-2-[(Phenylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
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-].[Na+].[Cl-].[C:20]1([N+]#N)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.NC1C=CC=CC=1.N([O-])=O.[Na+].Cl.[C:40](=[S:42])=[S:41]>CS(C)=O.O>[C:20]1([S:42][C:40]([N:2]2[CH:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)=[S:41])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
10
Reactant 7
Product 1
Reagents, catalysts & solvents 2
Procedure
(3RS)-1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid (3.24 g) is dissolved in dimethylsulfoxide (9 ml) and thereto is added 10N NaOH (33 ml) and further added carbon disulfide (0.91 ml) at room temperature. The mixture is stirred at room temperature for one hour, and to the mixture is added benzenediazonium chloride which is prepared from aniline (1.49 g), NaNO2 (1.15 g), conc. HCl (4.8 ml) and water (18.5 ml), and the mixture is stirred at 10° C. for one hour. The reaction mixture is treated in the same manner as described in Example 32. The product is crystallized from ethanol to give the title compound (676 mg) as pale yellow prisms, m.p. 167°-168° C. (decomp.).
Workup
- stirringthe mixture is stirred at 10° C. for one hour
- additionThe reaction mixture is treated in the same manner
- customThe product is crystallized from ethanol
Sources & evidence
- ORD record
- ord-50a04755e163489a8a424a87f0c1b357
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04628057
Reaction notes
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