Dimethyl Sulfoxide → HCID 21271528, compound

HRID 247351Notes

Reaction equation

HRID 247351 reaction equation
CS(C)=[O:3].Cl[CH2:6][CH2:7][CH:8]1[CH2:14][N:13]([CH3:15])[C:12](=[O:16])[C:11]2[CH:17]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:19]=[CH:20][C:10]=2[O:9]1.[NH:25]1[CH2:28][CH2:27][CH2:26]1.[C:29](=[O:32])([O-:31])[O-].[K+].[K+]>O>[C:12]([OH:16])(=[O:3])[C:29]([OH:31])=[O:32].[N:25]1([CH2:6][CH2:7][CH:8]2[CH2:14][N:13]([CH3:15])[C:12](=[O:16])[C:11]3[CH:17]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:19]=[CH:20][C:10]=3[O:9]2)[CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10422Azetidine2×HCID 11430Potassium CarbonateHCID 14098475HCID 14098475, compound

Product 1

HCID 21271528HCID 21271528, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of dimethyl sulfoxide was added 3.5 g (0.011 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-7-(trifluoromethyl)-1,4-benzoxazepin-5(4H)-one, 1.3 g (0.022 mole) of azetidine, and 10 g of potassium carbonate. The reaction mixture was stirred at room temperature for 24 hr and 1.18 g (0.021 mole) of azetidine was added. After 48 hr, the reaction mixture was poured into 500 ml of water and extracted with 3×100 ml of toluene. The combined organic extracts were washed with 2×150 ml of water, dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation. The residue was treated with oxalic acid in isopropyl alcohol to give 3.0 g (65%) of white analytically pure crystals, m.p. 163°-166° C.

Workup

  1. waitAfter 48 hr
  2. extractionextracted with 3×100 ml of toluene
  3. washThe combined organic extracts were washed with 2×150 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. additionThe residue was treated with oxalic acid in isopropyl alcohol
  8. customto give 3.0 g (65%) of white analytically pure crystals, m.p. 163°-166° C.

Sources & evidence

ORD record
ord-96efe78fff634d09af65a20b5323b55e
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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