Dimethyl Sulfoxide → HCID 21271463, compound

HRID 1193860Notes

Reaction equation

HRID 1193860 reaction equation
[Cl:1][C:2]1[C:12]([CH3:13])=[N:11][C:10]2[O:9][CH:8]([CH2:14][CH2:15]Cl)[CH2:7][N:6]([CH3:17])[C:5](=[S:18])[C:4]=2[CH:3]=1.[C:19](=[O:22])([O-:21])[O-].[Na+].[Na+].[NH:25]1[CH2:28][CH2:27][CH2:26]1.CS(C)=[O:31]>O>[OH2:9].[C:10]([OH:9])(=[O:31])[C:19]([OH:21])=[O:22].[N:25]1([CH2:15][CH2:14][CH:8]2[CH2:7][N:6]([CH3:17])[C:5](=[S:18])[C:4]3[CH:3]=[C:2]([Cl:1])[C:12]([CH3:13])=[N:11][C:10]=3[O:9]2)[CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10340Sodium CarbonateHCID 10422Azetidine2×HCID 14391508HCID 14391508, compound

Product 1

HCID 21271463HCID 21271463, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3.0 g (0.01 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 20 ml of dimethylsulfoxide was added ~5 g of sodium carbonate and 1.40 g (0.0245 mole) of azetidine. The reaction mixture was stirred for 2 days at room temperature and 0.3 g (0.005 mole) of azetidine was added and stirring continued for 3 days. The reaction mixture was poured in 300 ml of water. The aqueous mixture was extracted with 2×100 ml of benzene. The combined benzene extracts were washed with 3×75 ml of water, dried over sodium sulfate, filtered, and concentrated by rotary evaporation at 50° C. The residue was treated with oxalic acid in isopropyl alcohol which gave 3.5 g (82%) of yellow analytically pure crystals, m.p. 162°-66° C. with decomposition.

Workup

  1. stirringstirring
  2. waitcontinued for 3 days
  3. extractionThe aqueous mixture was extracted with 2×100 ml of benzene
  4. washThe combined benzene extracts were washed with 3×75 ml of water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation at 50° C
  8. additionThe residue was treated with oxalic acid in isopropyl alcohol which
  9. customgave 3.5 g (82%) of yellow analytically pure crystals, m.p. 162°-66° C. with decomposition

Sources & evidence

ORD record
ord-b02872320bee4ebfbb944724596e8801
Source dataset
uspto-grants-1989_03
Patent number
US04810795

Reaction notes

Loading…