Triethylamine → 4-Chloro-5-cyclopentyloxy-2-fluorophenylisocyanate

HRID 2225946Notes

Reaction equation

HRID 2225946 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[F:9][C:10]1[CH:16]=[C:15]([Cl:17])[C:14]([O:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:13][C:11]=1[NH2:12].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:9][C:10]1[CH:16]=[C:15]([Cl:17])[C:14]([O:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:13][C:11]=1[N:12]=[C:2]=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 152793894-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

Product 1

HCID 544415444-Chloro-5-cyclopentyloxy-2-fluorophenylisocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
0 °C

Procedure

The mixture of trichloromethyl chloroformate (530 ml, 4.4 mol) and toluene (4 liters) were put in a 10-liter three-neck flask as equipped with a stirrer, a dropping funnel, and a reflux condenser, and cooled to 0° C. To the solution was dropwise added a toluene solution (1 liter) containing 2-fluoro-4-chloro-5-cyclopentyloxyaniline (1.0 kg, 2.86 mol) and triethylamine (20 ml) over a period of 8 hours. After addition, the reaction solution was stirred under heat at about 100° C. After reaction, toluene was removed by distillation, and the impurities as precipitated out were removed by filtration. As a result, 2-fluoro-4-chloro-5-cyclopentyloxyphenylisocyanate was obtained almost quantitatively. Spectral data and other data of the product are those as shown in Example 24.

Workup

  1. customwere put in a 10-liter three-neck flask
  2. customas equipped with a stirrer, a dropping funnel, and a reflux condenser
  3. additionAfter addition
  4. temperatureunder heat at about 100° C
  5. customwas removed by distillation
  6. customthe impurities as precipitated out
  7. customwere removed by filtration

Sources & evidence

ORD record
ord-682f3ff987104548881d3eb2226dc050
Source dataset
uspto-grants-1994_09
Patent number
US05344953

Reaction notes

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