Dimethyl Sulfoxide → HCID 13561925, compound

HRID 1249031Notes

Reaction equation

HRID 1249031 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+].CS(C)=O.[CH:23]1(Br)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[C:30](=[S:32])=[S:31]>O>[CH:23]1([S:32][C:30]([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:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6348Carbon DisulfideHCID 7960Cyclohexyl bromideHCID 14798Sodium HydroxideHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 13561925HCID 13561925, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In the same manner as described in Example 6, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (4.32 g), NaOH (1.8 g), dimethylsulfoxide (25 ml), water (2 ml), carbon disulfide (1.45 ml) and cyclohexyl bromide (3.9 g) are reacted and treated. The product is crystallized from chloroform-n-hexane to give the title compound (4.5 g, 61%), m.p. 150.5°-151° C.

Workup

  1. customare reacted
  2. additiontreated
  3. customThe product is crystallized from chloroform-n-hexane

Sources & evidence

ORD record
ord-dd9686fb27c44b2781ac594c378451d0
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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