1,1'-Carbonyldiimidazole → HCID 15053388, compound

HRID 2081413Notes

Reaction equation

HRID 2081413 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].[F:13][C:14]([F:27])([F:26])[C:15]1[CH:25]=[CH:24][C:18]([O:19]C2CNC2)=[CH:17][CH:16]=1>O1CCCC1.O.C1C=CC=CC=1>[F:13][C:14]([F:26])([F:27])[C:15]1[CH:25]=[CH:24][C:18]([O:19][CH:11]2[CH2:9][N:8]([C:1]([N:3]3[CH:7]=[CH:6][N:5]=[CH:4]3)=[O:2])[CH2:12]2)=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 128124993-[4-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 15053388HCID 15053388, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.7 g (0.01 mole) 1,1'-carbonyldiimidazole in 50 ml of tetrahydrofuran and 3 g (0.015 mole) of 3-[4-(trifluoromethyl)phenoxy]azetidine was stirred for 6 hr. The reaction mixture was diluted with water and extracted with 3×50 ml of methylene chloride. The extracts upon concentrating in vacuo gave an amber residue which was dissolved in 20 ml of benzene and washed with dilute hydrochloric acid, then washed with water. The benzene portion was concentrated to give a semi-solid residue which when triturated with isopropyl ether gave 1.4 g of gray material. Recrystallization from acetonitrile gave 1.3 g (41.8%) of fine gray crystals, m.p. 139°-140° C.

Workup

  1. extractionextracted with 3×50 ml of methylene chloride
  2. concentrationupon concentrating in vacuo
  3. customgave an amber residue which
  4. washwashed with dilute hydrochloric acid
  5. washwashed with water
  6. concentrationThe benzene portion was concentrated
  7. customto give a semi-solid residue which when
  8. customtriturated with isopropyl ether

Sources & evidence

ORD record
ord-d0fd77fdecbe47d6bdd0960c81833ded
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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