Acetonitrile → HCID 14098476, compound

HRID 247301Notes

Reaction equation

HRID 247301 reaction equation
C(#N)C.[Cl:4][CH2:5][CH2:6][CH:7]1[CH2:13][N:12]([CH3:14])[C:11](=O)[C:10]2[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:9]=2[O:8]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:25]>C1(C)C=CC=CC=1>[Cl:4][CH2:5][CH2:6][CH:7]1[CH2:13][N:12]([CH3:14])[C:11](=[S:25])[C:10]2[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:9]=2[O:8]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14817Phosphorus sulfide (P2S5)HCID 14098475HCID 14098475, compound

Product 1

HCID 14098476HCID 14098476, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 30 ml of acetonitrile was added 1.25 g (0.004 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-7-(trifluoromethyl)-1,4-benzoxazepine-5(4H)-one and 0.92 g (0.002 mole) of phosphorus pentasulfide and the reaction mixture heated to reflux for 4 hr. After cooling, 30-40 ml of toluene was added and the mixture filtered. The filtrate was washed with 3×50 ml of saturated potassium carbonate, charcoaled, filtered, and concentrated by rotary evaporation. The residue was crystallized from isopropyl ether to give 0.65 g (50%) of yellow, analytically pure crystals, m.p., 146°-48° C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 4 hr
  3. temperatureAfter cooling
  4. filtrationthe mixture filtered
  5. washThe filtrate was washed with 3×50 ml of saturated potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was crystallized from isopropyl ether
  9. customto give 0.65 g (50%) of yellow, analytically pure crystals
  10. customm.p., 146°-48° C.

Sources & evidence

ORD record
ord-e9d5b08216da4c9fbd24fa6115015e06
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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