Dimethylformamide → 3-Chloro-1-methyl-1,2-dihydroquinoxalin-2-one

HRID 979463

Reaction equation

HRID 979463 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=O)[C:3]1=[O:13].CN(C=O)C.S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:21][C:4]1[C:3](=[O:13])[N:2]([CH3:1])[C:11]2[C:6]([N:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 6006271-Methyl-1,4-dihydro-2,3-quinoxalinedione

Product 1

HCID 14710883-Chloro-1-methyl-1,2-dihydroquinoxalin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 56.1 g. (0.32 m.) of 1,4-dihydro-1-methylquinoxalin-2,3-dione, 10 ml. of DMF, 50 ml. (0.67 m.) of thionyl chloride and 1 l. of toluene was refluxed for 1 hour, cooled, and stripped, finally under high vacuum to a crude dark solid, m.p. 124°-130° C. of sufficient purity to use in the next step.

Workup

  1. additionA mixture of 56.1 g
  2. temperaturecooled

Sources & evidence

ORD record
ord-09d9ee2c8d7d469888f7ac08171b223c
Source dataset
uspto-grants-1987_05
Patent number
US04668678

Linked notes

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