Sulfuryl chloride → 7-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one

HRID 4815

Reaction equation

HRID 4815 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[O:6]1.S(Cl)([Cl:21])(=O)=O>CN(C)C=O>[Cl:21][C:15]1[CH:16]=[N:17][C:7]2[O:6][CH:5]([CH2:4][CH2:3][Cl:2])[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[C:8]=2[CH:14]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 137264372-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)one hydrochloride

Product 1

HCID 137264457-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-oneYield 6.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A sample of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5-(4H)-one hydrochloride (10 g, 136 mole) was dissolved in dimethylformamide (150 ml) and heated to reflux. Sulfuryl chloride (20 g, 0.148 mole) was then added dropwise over a period of 40-50 minutes. The reaction was allowed to stir at reflux for 30 minutes following the addition of SO2CL2. After cooling, the contents of the flask were partitioned between water (150 ml) and benzene (150 ml). The benzene layer was saved and the water layer extracted with an additional amount of benzene (2×50 ml). The benzene extracts were combined and washed with dilute aqueous potassium hydroxide (2×50 ml) followed by dilute aqueous hydrochloric acid (2×50 ml). The benzene layer was dried over sodium sulfate and concentrated by rotary evaporation (~70° C., water aspirator) yielding 2.61 g of crude material. The crude material was recrystallized from isopropyl ether giving 1.25 g (12.6%) of off-white crystals, m.p. 78°-79° C.

Workup

  1. temperatureheated to reflux
  2. temperatureat reflux for 30 minutes
  3. additionthe addition of SO2CL2
  4. temperatureAfter cooling
  5. customthe contents of the flask were partitioned between water (150 ml) and benzene (150 ml)
  6. extractionthe water layer extracted with an additional amount of benzene (2×50 ml)
  7. washwashed with dilute aqueous potassium hydroxide (2×50 ml)
  8. dry with materialThe benzene layer was dried over sodium sulfate
  9. concentrationconcentrated by rotary evaporation (~70° C., water aspirator)

Sources & evidence

ORD record
ord-11860a3dcb584788ab48608c74e8cc2e
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Linked notes

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