Diphenylmethane → N-(2-Propenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide

HRID 2081392Notes

Reaction equation

HRID 2081392 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.C1(CC2C=CC=CC=2)C=CC=CC=1.[CH2:29]([N:32]=[C:33]=[O:34])[CH:30]=[CH2:31]>C(OC(C)C)(C)C>[CH2:29]([NH:32][C:33]([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:34])[CH:30]=[CH2:31]

Participants

5

Reactant 3

HCID 7580DiphenylmethaneHCID 15123Allyl isocyanateHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 15053417N-(2-Propenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamideYield 63.3%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A solution of 18.9 g (0.05 mole) of crude 3-[3-(trifluoromethyl)phenoxy]azetidine (contains an equal molar amount of diphenylmethane) in 100 ml of isopropyl ether was stirred under nitrogen while 4.16 g (0.05 mole) of 2-propenyl isocyanate was slowly added. The reaction mixture which was somewhat turbid, cleared and after 1 hr a fine crystalline precipitate began to form. After stirring for 18 hrs, the product was removed by filtration, washed with fresh isopropyl ether and air dried to yield 9.5 g of white crystals, m.p. 75°-76° C.

Workup

  1. additionwas slowly added
  2. customto form
  3. customthe product was removed by filtration
  4. washwashed with fresh isopropyl ether and air
  5. customdried

Sources & evidence

ORD record
ord-3f353e90edec4398a2d1e76e82186182
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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