Dimethyl Sulfoxide → HCID 21271489, compound

HRID 1194264Notes

Reaction equation

HRID 1194264 reaction equation
C[S:2]([CH3:4])=[O:3].Cl[CH2:6][CH2:7][CH:8]1[CH2:14][N:13]([CH3:15])[C:12](=S)[C:11]2[CH:17]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:19]=C[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:10]([OH:9])(=[O:3])[C:29]([OH:31])=[O:32].[N:25]1([CH2:6][CH2:7][CH:8]2[CH2:14][N:13]([CH3:15])[CH:12]3[C:4](=[S:2])[CH:19]=[C:18]([C:21]([F:22])([F:23])[F:24])[CH:17]=[C:11]3[O:9]2)[CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10422Azetidine2×HCID 11430Potassium CarbonateHCID 14098476HCID 14098476, compound

Product 1

HCID 21271489HCID 21271489, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of dimethylsulfoxide was added 4.0 g (0.012 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-7-(trifluoromethyl)-1,4-benzoxazepine-5(4H)-thione 1.4 g (0.025 mole) of azetidine and 10 g of potassium carbonate. The reaction mixture was stirred at room temperature for 2 days and 1.2 g (0.021 mole) of azetidine was added. After 3 days, the entire reaction mixture was poured into 500 ml of water and extracted with 3×100 ml of toluene. The combined organic layers were washed with 2×100 ml of water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The solid residue was treated with oxalic acid in isopropyl alcohol to give 2.4 g (46%) of yellow crystals, m.p. 96°-110° C.

Workup

  1. waitAfter 3 days
  2. customthe entire reaction mixture
  3. extractionextracted with 3×100 ml of toluene
  4. washThe combined organic layers were washed with 2×100 ml of water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. additionThe solid residue was treated with oxalic acid in isopropyl alcohol

Sources & evidence

ORD record
ord-f3e854d21a8e451db00f2a0bd3fddca4
Source dataset
uspto-grants-1989_03
Patent number
US04812565

Reaction notes

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