2-Mercaptoacetamide → HCID 3207460, compound

HRID 2413324Notes

Reaction equation

HRID 2413324 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:16][CH3:17])=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.[SH:18][CH2:19][C:20]([NH2:22])=[O:21].[OH-].[K+]>CN(C)C=O.O>[NH2:13][C:12]1[C:11]2[C:2](=[N:3][C:4]3[C:9]([CH:10]=2)=[CH:8][C:7]([O:14][CH3:15])=[C:6]([O:16][CH3:17])[CH:5]=3)[S:18][C:19]=1[C:20]([NH2:22])=[O:21]

Participants

6

Reactant 3

HCID 129612-MercaptoacetamideHCID 14797Potassium HydroxideHCID 133595612-Chloro-6,7-dimethoxyquinoline-3-carbonitrile

Product 1

HCID 3207460HCID 3207460, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 20 g of 2-chloro-6,7-dimethoxy-3-quinolinecarbonitrile in 500 ml of dimethylformamide was added 20 g of 2-mercaptoacetamide. To the resultant mixture was added dropwise a solution of 15 g of potassium hydroxide in 100 ml of water. The mixture was stirred at room temperature for 30 minutes and enough additional water was added to give a homogeneous solution. The mixture was stirred at room temperature for 16 hours and then poured into 4 liters of water. The yellow precipitate which formed was separated by filtration and dried to give 3-amino-6,7-dimethoxy thieno[2,3-b]quinoline-2-carboxamide melting at about 278.5°-279.5° C. with decomposition.

Workup

  1. customto give a homogeneous solution
  2. stirringThe mixture was stirred at room temperature for 16 hours
  3. customThe yellow precipitate which formed
  4. customwas separated by filtration
  5. customdried

Sources & evidence

ORD record
ord-df72e06de6e64ecca2a807b50453544d
Source dataset
uspto-grants-1985_01
Patent number
US04496725

Reaction notes

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