Dimethyl Sulfoxide → 2-(1-Azetidinyl]ethyl-7-chloro-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione oxalate

HRID 247341Notes

Reaction equation

HRID 247341 reaction equation
[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14]Cl)[CH2:7][N:6]([CH3:16])[C:5](=[S:17])[C:4]=2[CH:3]=1.[C:18](=[O:21])([O-:20])[O-].[K+].[K+].[NH:24]1[CH2:27][CH2:26][CH2:25]1.CS(C)=[O:30]>O>[C:10]([OH:9])(=[O:30])[C:18]([OH:20])=[O:21].[N:24]1([CH2:14][CH2:13][CH:8]2[CH2:7][N:6]([CH3:16])[C:5](=[S:17])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:12]=[N:11][C:10]=3[O:9]2)[CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10422Azetidine3×HCID 11430Potassium CarbonateHCID 137264487-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)thione

Product 1

HCID 137266202-(1-Azetidinyl]ethyl-7-chloro-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione oxalateYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4.75 g (0.0164 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 40 ml of dimethyl sulfoxide was added 8.0 g of crushed potassium carbonate and 1.4 g (0.0246 mole) of azetidine. The flask was sealed and stirred at room temperature for 24 hr after which an additional 0.6 g (0.011 mole) of azetidine was added. After 24 hr, another 0.5 (0.009 mole) of azetidine was added and stirring continued at room temperature. After 48 hr, the entire reaction mixture was diluted with 200 ml of water and extracted with 2×100 ml of benzene. The organic extracts were combined, washed with 3×100 ml of water and 1×100 ml saturated sodium chloride, dried over sodium sulfate, filtered, and concentrated by rotary evaporation (65° C., 30 mm Hg). The residue was treated with oxalic acid in isopropyl alcohol to give 5.4 g (82%) of yellow crystals, m.p. 146°-150° C.

Workup

  1. customThe flask was sealed
  2. additionwas added
  3. customcontinued at room temperature
  4. waitAfter 48 hr
  5. customthe entire reaction mixture
  6. extractionextracted with 2×100 ml of benzene
  7. washwashed with 3×100 ml of water and 1×100 ml saturated sodium chloride
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated by rotary evaporation (65° C., 30 mm Hg)
  11. additionThe residue was treated with oxalic acid in isopropyl alcohol

Sources & evidence

ORD record
ord-3f1eef69ac9c4a6494925e917fccd025
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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