2-Chloroethyl methyl sulfide → 2-Chloro-5-[2-(methylsulfanyl)ethyl]pyrido[2,3-b][1,4]benzoxazepin-6(5H)-one

HRID 1078205Notes

Reaction equation

HRID 1078205 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[O:7][C:6]=2[N:17]=1.C1CCC(=C(F)CNCC2C=CC(F)=CC=2)CC1.[H-].[Na+].Cl[CH2:39][CH2:40][S:41][CH3:42]>O.CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:39][CH2:40][S:41][CH3:42])[C:10](=[O:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[O:7][C:6]=2[N:17]=1

Participants

7

Reactant 4

HCID 109652-Chloroethyl methyl sulfideHCID 24758Sodium hydrideHCID 19429156HCID 19429156, compoundHCID 23646094HCID 23646094, compound

Product 1

HCID 4539562-Chloro-5-[2-(methylsulfanyl)ethyl]pyrido[2,3-b][1,4]benzoxazepin-6(5H)-oneYield 78.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

To as suspension of 17.0g (0.069 mole) 2-Chloropyrido[2,3-b][1,4]benzoxazepin-6(5H)-one and 150 mL of N,N-dimethylacetamide was added 9.8g of sodium hydride (50%). The mixture was warmed to 60° C. for 30 minutes. To the reaction mixture 12.2g (0.11 mole) of 2-chloroethylmethylsulfide was added dropwise. The mixture was heated to 120° C. for 4 hours, then cooled to room temperature and poured into water. The crude product was purified by column chromatography using silica gel and then recrystallized from petroleum ether/benzene to yield 17.3g (78% yield) of 2-chloro-5-(methylthioethyl)pyrido[2,3-b][1,4]benzoxazepin-6(5H)-one, m.p. 126°-128° C.

Workup

  1. temperatureThe mixture was heated to 120° C. for 4 hours
  2. temperaturecooled to room temperature
  3. customThe crude product was purified by column chromatography
  4. customrecrystallized from petroleum ether/benzene

Sources & evidence

ORD record
ord-6518c709488845f0a092026b71efb9e4
Source dataset
uspto-grants-1996_08
Patent number
US05547951

Reaction notes

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