2-Bromoethanol → HCID 23287654, compound

HRID 367212Notes

Reaction equation

HRID 367212 reaction equation
[H-].[Li+].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([NH:8][C:9]2[S:10][C:11]3[N:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)=[CH:6][CH:5]=1.Br[CH2:23][CH2:24][OH:25]>CN(C=O)C>[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([N:8]=[C:9]2[N:14]([CH2:23][CH2:24][OH:25])[C:13](=[O:15])[C:12]3[CH:16]=[CH:17][CH:18]=[N:19][C:11]=3[S:10]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 62714Lithium hydrideHCID 42920704H-Pyrido[3,2-e]-1,3-thiazin-4-one, 2-[(4-chlorophenyl)amino]-2×

Product 1

HCID 23287654HCID 23287654, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

In an atmosphere of argon, a mixture of 60 mg (7.6 mmol) of lithium hydride and 10 ml of DMF was put in a 100 ml flask. To the flask was then connected a dropping funnel which contained 1,600 mg (5.5 mmol) of 2-(4-chloroanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one and 10 ml of DMF. The solution of 2-(4-chloroanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one was then added dropwise to the aforementioned mixture with stirring in 5 minutes. The mixture was further stirred for 2 hours. To the mixture was then added a mixture of 1,034 mg of 2-bromoethanol and 4 ml of DMF. The mixture was then stirred for 22 hours. After the termination of reaction, the mixture was concentrated under reduced pressure. The resulting residue was then extracted with water and ethyl acetate. The resulting organic phase was separated, washed with water and saturated brine, and then dried over sodium sulfate. The drying agent was then removed by filtration. The filtrate was then concentrated under reduced pressure. The resulting residue was then purified through silica gel column chromatography (eluant: 1/1 mixture of ethyl acetate and normal hexane). As a result, 1.48 g of 2,3-dihydro-2-[(4-chlorophenyl)imino]-3-(2-hydroxyethyl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one was obtained as a low polarity substance, and 220 mg of 2-[N-(4-chlorophenyl)-N-(2-hydroxyethyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one was obtained as a high polarity substance.

Workup

  1. customwas put in a 100 ml flask
  2. stirringThe mixture was further stirred for 2 hours
  3. additionTo the mixture was then added
  4. stirringThe mixture was then stirred for 22 hours
  5. customAfter the termination of reaction
  6. concentrationthe mixture was concentrated under reduced pressure
  7. extractionThe resulting residue was then extracted with water and ethyl acetate
  8. customThe resulting organic phase was separated
  9. washwashed with water and saturated brine
  10. dry with materialdried over sodium sulfate
  11. customThe drying agent was then removed by filtration
  12. concentrationThe filtrate was then concentrated under reduced pressure
  13. customThe resulting residue was then purified through silica gel column chromatography (eluant: 1/1 mixture of ethyl acetate and normal hexane)

Sources & evidence

ORD record
ord-68e7dadbd21944bd85ae9bee904fae61
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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