Benzyl isocyanate → HCID 15053416, compound

HRID 2081390Notes

Reaction equation

HRID 2081390 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH:7]1[CH2:10][NH:9][CH2:8]1.[CH2:16]([N:23]=[C:24]=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:17]1([CH2:16][NH:23][C:24]([N:9]2[CH2:10][CH:7]([O:6][C:5]3[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=3)[CH2:8]2)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 15053416HCID 15053416, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and chilled (10°-20° C.) solution of 0.04 mole of 3-[3-(trifluoromethyl)phenoxy]azetidine in 100 ml of methylene chloride was added dropwise 6.12 g (0.046 mole) of benzyl isocyanate. The reaction mixture was stirred at room temperature for 2 hr and was filtered. The filter cake was washed with petroleum ether (2×50 ml), dilute aqueous sodium bicarbonate (2×50 ml), and water (2×50 ml), yielding 12 g (86%). Recrystallization twice from ethyl acetate gave 9.0 g of clear white flakes, m.p. 173.5°-175° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hr
  2. filtrationwas filtered
  3. washThe filter cake was washed with petroleum ether (2×50 ml), dilute aqueous sodium bicarbonate (2×50 ml), and water (2×50 ml)
  4. customyielding 12 g (86%)
  5. customRecrystallization twice from ethyl acetate
  6. customgave 9.0 g of clear white flakes, m.p. 173.5°-175° C.

Sources & evidence

ORD record
ord-e152cbdb601f474eb38b0c8c3f95c924
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

Loading…