Isopropyl isocyanate → HCID 19799637, compound

HRID 2081422Notes

Reaction equation

HRID 2081422 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.[CH:16]([N:19]=[C:20]=[O:21])([CH3:18])[CH3:17]>C(Cl)Cl>[CH3:17][CH:16]([NH:19][C:20]([N:9]1[CH2:10][CH:7]([O:6][C:5]2[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=2)[CH2:8]1)=[O:21])[CH3:18]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 19799637HCID 19799637, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and chilled (10°-20° C.) solution of 9.0 g (0.042 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine in 100 ml of dry methylene chloride was added dropwise 4.1 g (0.048 mole) of isopropyl isocyanate. The reaction mixture was stirred at room temperature for 2 hr and was diluted with 100 ml of methylene chloride. The solution was washed with 5% sodium hydroxide (2×40 ml), water (50 ml), saturated sodium chloride (50 ml), dried (sodium sulfate) and concentrated in vacuo. The residue was crystallized from ethyl acetate, affording 7.6 g (60.6%). Recrystallization from ethyl acetate gave 5.0 g of clear white needles, m.p. 150°-151.5° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hr
  2. washThe solution was washed with 5% sodium hydroxide (2×40 ml), water (50 ml), saturated sodium chloride (50 ml)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from ethyl acetate
  6. customaffording 7.6 g (60.6%)
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-8153ed7a999842bab88b5fda632add90
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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