4-Chlorophenyl Isocyanate → HCID 15053436, compound

HRID 974602Notes

Reaction equation

HRID 974602 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:21])([F:20])[C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[O:12][CH:13]1[CH2:16][NH:15][CH2:14]1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1.C(N(CC)CC)C>O1CCCC1.O>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([N:15]2[CH2:16][CH:13]([O:12][C:11]3[CH:17]=[CH:18][CH:19]=[C:9]([C:8]([F:7])([F:20])[F:21])[CH:10]=3)[CH2:14]2)=[O:31])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 19799580HCID 19799580, compound

Product 1

HCID 15053436HCID 15053436, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.4 g (0.02 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine oxalate [1:1] and 3.38 g (0.022 mole) of 4-chlorophenyl isocyanate was stirred in 20 ml of tetrahydrofuran for 15 min then treated with 5 ml of triethylamine. The reaction mixture was exothermic and was stirred for 18 hr as it cooled to ambient temperature. The reaction mixture was diluted with 100 ml of water and the residue which separated solidified. Filtration yielded 8.9 g of crude wet solid. Recrystallization from methyl isobutyl ketone and 30/60 petroleum ether yielded 3.65 g (49.7%) of fine white crystals, m.p. 138°-140° C.

Workup

  1. customthe residue which separated
  2. filtrationFiltration
  3. customyielded 8.9 g of crude wet solid
  4. customRecrystallization from methyl isobutyl ketone and 30/60 petroleum ether

Sources & evidence

ORD record
ord-7aee0a23eaa94793a2eb0ee4926f627f
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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