Dimethylformamide → 2,3-dihydro-2,5-dimethyl-3-oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile

HRID 27745Notes

Reaction equation

HRID 27745 reaction equation
O=C1NC=[C:5]2[S:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[NH:9][C:4]2=[C:3]1[C:16]#[N:17].I[CH3:19].[CH3:20][N:21]([CH3:24])[CH:22]=[O:23]>O>[CH3:20][N:21]1[C:22](=[O:23])[C:3]([C:16]#[N:17])=[C:4]2[C:5]([S:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[N:9]2[CH3:19])=[CH:24]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 125702342,3-dihydro-3-oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile

Product 1

HCID 233420122,3-dihydro-2,5-dimethyl-3-oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 parts of 2,3-dihydro-3oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile, 45 parts of iodomethane, and 95 parts of N,N-dimethylformamide is heated at 100° for 2 hours, then diluted with 100 parts of water. The precipitate which forms is filtered out, dried in vacuo, and recrystallized from ethanol to give 2,3-dihydro-2,5-dimethyl-3-oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile melting at approximately 236°-237°.

Workup

  1. temperatureis heated at 100° for 2 hours
  2. filtrationThe precipitate which forms is filtered out
  3. customdried in vacuo
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-af2db1a877d349b0b30c7325e13f017e
Source dataset
uspto-grants-1980_09
Patent number
US04223136

Reaction notes

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