Dimethylformamide → HCID 23287589, compound

HRID 367190Notes

Reaction equation

HRID 367190 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:23])[C:11]([NH:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2F)=[S:12])=[CH:6][CH:5]=1.CN(C=O)C>C1COCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:11]2[S:12][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:15]=3[C:14](=[O:22])[N:13]=2)[CH3:23])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 23287615HCID 23287615, compound

Product 1

HCID 23287589HCID 23287589, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of argon, a suspension of 167 mg of sodium hydride (60% oil suspension) in 1 ml of THF was added to a mixture of 1.230 g (3.80 mmol) of 1-(4-chlorophenyl)-3-(3-fluoroisonicotinoyl)-1-methylthiourea and 10 ml of DMF while being cooled over a water bath. The mixture was stirred for 10 minutes, and then stirred over a 110° C. oil bath for 5 hours. The reaction mixture was allowed to cool, and then concentrated under reduced pressure. The resulting residue was then poured into ice-water. The resulting precipitate was collected by filtration, washed with water, and then dried under reduced pressure. The resulting crude product was then recrystallized from ethanol to obtain 802 mg of 2-[N-(4-chlorophenyl)-N-methylamino]-4H-pyrido[4,3-e]-1,3-thiazin-4-one.

Workup

  1. temperaturewhile being cooled over a water bath
  2. stirringstirred over a 110° C. oil bath for 5 hours
  3. temperatureto cool
  4. concentrationconcentrated under reduced pressure
  5. additionThe resulting residue was then poured into ice-water
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure
  9. customThe resulting crude product was then recrystallized from ethanol

Sources & evidence

ORD record
ord-1f798ba6197f42388cda1a0be5d997ba
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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