Phosgene → HCID 18677138, compound

HRID 1634086Notes

Reaction equation

HRID 1634086 reaction equation
CN1CC[O:5][CH2:4]C1.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([C:24]([F:27])([F:26])[F:25])=[N:16]2)=[CH:11][CH:10]=1.C(Cl)(Cl)=O>C(Cl)Cl>[N:8]([C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:19]([C:20]([F:21])([F:22])[F:23])=[CH:18][C:17]([C:24]([F:27])([F:26])[F:25])=[N:16]2)=[CH:13][CH:14]=1)=[C:4]=[O:5]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 79724-MethylmorpholineHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)aniline

Product 1

HCID 18677138HCID 18677138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To morpholinomethyl polystyrene (Novabiochem, substitution=3.55 mmol/g, 1.02 g, 3.62 mmol) in methylene chloride (18.5 mL) under argon was added 1-(4′-aminophenyl)-3,5-bis(trifluoromethyl)pyrazole (0.555 g, 1.88 mmol). The mixture was cooled to 0° C. and phosgene (1.93M in toluene, Fluka, 1.95 mL, 3.76 mmol) was added. After thirty minutes the reaction mixture was filtered, washed with methylene chloride (2×30 mL) and concentrated to give 1-(4′-isocyanatophenyl)-3,5-bis(trifluoromethyl)pyrazole.

Workup

  1. filtrationAfter thirty minutes the reaction mixture was filtered
  2. washwashed with methylene chloride (2×30 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-17fdbf03f23844bca382331c71a1304c
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

Loading…