Carbon Disulfide → HCID 13561953, compound

HRID 1249052

Reaction equation

HRID 1249052 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][C@H:3]([C:14]([OH:16])=[O:15])[NH:2]1.[OH-].[K+].[CH2:19](Cl)[C:20]1[O:24][CH:23]=[CH:22][CH:21]=1.C(O)C1OC=CC=1.S(Cl)(Cl)=O.[C:37](=[S:39])=[S:38]>N1C=CC=CC=1.C(O)C>[CH2:19]([S:39][C:37]([N:2]1[C@@H: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:38])[C:20]1[O:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 6

HCID 6348Carbon DisulfideHCID 7361Furfuryl AlcoholHCID 14797Potassium HydroxideHCID 24386Thionyl ChlorideHCID 2195202-(Chloromethyl)furanHCID 675102D-1,2,3,4-Tetrahydronorharman-3-carboxylic acid

Product 1

HCID 13561953HCID 13561953, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

In the same manner as descsribed in Example 32, (3R)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (8.65 g), KOH (4.67 g), carbon disulfide (2.43 ml), 75% ethanol (120 ml) and furfuryl chloride which is prepared from furfuryl alcohol (9.24 g), thionyl chloride (12.34 g) and pyridine (8.94 g) are reacted and treated to give the title compound (2.31 g) as pale yellow powder.

Workup

  1. customare reacted
  2. additiontreated

Sources & evidence

ORD record
ord-4d04b1f0650b4fee9de48418bb2f4bae
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Linked notes

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