Phosgene → HCID 10130869, compound

HRID 2307224Notes

Reaction equation

HRID 2307224 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][N:10](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:9]2)=[CH:4][CH:3]=1.[C:25](Cl)(Cl)=[O:26]>ClCCl.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][N:10]([C:25]([NH:10][CH2:9][CH:8]=[CH2:5])=[O:26])[CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 22605396HCID 22605396, compound

Product 1

HCID 10130869HCID 10130869, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(4-fluorophenyl)-N-(diphenylnethyl)azetidine (17) (0.67 g) in dichloromethane (5 mL) at 0° C. was added dropwise a solution of 20% phosgene in toluene (2.5 mL). The mixture was stirred for 90 minutes then concentrated in vacuo. To the concentrate was added dichloromethafe (5 mL) and to this solution at 0° C. was added, dropwise, with stirring, allylamine (0.5 mL). The mixture was stirred for 18 hrs at room temperature, diluted with dichloromethane (20 mL), washed (water. brine), dried (Na2SO4) and concentrated in vacuo. Recrystallisation from diisopropyl ether gave 3-(4-(fluorophenyl)-N-(2-propeny)azetidine-1-carboxamide (18) (0.30 g), m.p. 119-120° C. (diisopropyl ether). Found: C, 66.61; H, 6.37; N, 11.74. C13H15FN2O requires C, 66.65; H. 6.45; N, 11.95%.

Workup

  1. concentrationthen concentrated in vacuo
  2. additionTo the concentrate was added dichloromethafe (5 mL)
  3. additionto this solution at 0° C. was added
  4. stirringdropwise, with stirring
  5. stirringThe mixture was stirred for 18 hrs at room temperature
  6. additiondiluted with dichloromethane (20 mL)
  7. washwashed (water. brine)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customRecrystallisation from diisopropyl ether

Sources & evidence

ORD record
ord-cfbeee07e438421a86b6e8b605f94c0a
Source dataset
uspto-grants-2004_12
Patent number
US06831078B1

Reaction notes

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