1,1'-Carbonyldiimidazole → HCID 15053372, compound

HRID 1886598Notes

Reaction equation

HRID 1886598 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=[CH:4]1)=[O:2].[CH2:13](N)/[CH:14]=C/C.C(O)(=O)C(O)=O.[F:24][C:25]([F:38])([F:37])[C:26]1[CH:36]=[CH:35][C:29]([O:30]C2CNC2)=[CH:28][CH:27]=1>C(N(CC)CC)C>[CH2:12]([NH:8][C:1]([N:3]1[CH2:4][CH:6]([O:30][C:29]2[CH:35]=[CH:36][C:26]([C:25]([F:24])([F:37])[F:38])=[CH:27][CH:28]=2)[CH2:7]1)=[O:2])/[CH:11]=[CH:13]/[CH3:14]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 643377221035-54-1HCID 128125003-[4-(Trifluoromethyl)phenoxy]azetidine oxalate

Product 1

HCID 15053372HCID 15053372, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 3.6 g (0.022 mole) of 1,1'-carbonyldiimidazole and 1.6 g (0.022 mole) of trans-crotylamine was stirred for 1 hr, then treated with 6.2 g (0.02 mole) of 3-[4-(trifluoromethyl)phenoxy]azetidine oxalate and followed in 0.5 hr with 5 ml of triethylamine with stirring continued for 16 hr. The partially crystalline mixture was washed with 2×50 ml of water, dried over magnesium sulfate and concentrated on a rotary evaporator to a solid residue, 14.2 g. Recrystallization from methanol-water yielded 5.35 g (85.1%) of fine white crystals, m.p. 157°-158° C.

Workup

  1. stirringwith stirring
  2. waitcontinued for 16 hr
  3. washThe partially crystalline mixture was washed with 2×50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated on a rotary evaporator to a solid residue, 14.2 g
  6. customRecrystallization from methanol-water

Sources & evidence

ORD record
ord-4173531b04894c8488a8d92cdc836b56
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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