Carbon Disulfide → HCID 13561942, compound

HRID 1249049Notes

Reaction equation

HRID 1249049 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+].[C:19](=[S:21])=[S:20].Br[CH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1>CS(C)=O>[C:28]([C:27]1[CH:31]=[CH:32][C:24]([CH2:23][S:20][C:19]([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:21])=[CH:25][CH:26]=1)([OH:30])=[O:29]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 225994-(Bromomethyl)benzoic acidHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 13561942HCID 13561942, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as described in Example 16, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1.08 g), 10N NaOH (1.5 ml), carbon disulfide (456 mg), dimethylsulfoxide and 4-bromomethylbenzoic acid (1.29 g) are reacted and treated. The product is crystallized from chloroform to give the title compound (1.23 g, 53%), m.p. 152°-153° C. (decomp.).

Workup

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

Sources & evidence

ORD record
ord-e456381c4eb14d6682d6e331c06eb8a6
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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