Phosgene → HCID 86740301, compound

HRID 1719618Notes

Reaction equation

HRID 1719618 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH2:5]([O:12][C:13]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(C)[C:14](O)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O.C1(C)C=CC=CC=1>[CH2:5]([O:12][CH:13]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:14][C:1]([Cl:4])=[O:2])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 6371Phosgene7×HCID 70459432HCID 70459432, compound

Product 1

HCID 86740301HCID 86740301, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A three-liter, round-bottom flask was obtained and fitted with an overhead stirrer, a thermocouple, a temperature controller, an addition funnel with a cold trap overhead, and a line leading to a phosgene cyclinder. Also it was fitted with an exit line to a nitrogen/vacuum source, a heating mantle, and a catch basin. The exit line went to a condenser and a caustic scrubber. Into this flask was placed 183.2 g (0.67 mole) benzyloxyphenoxypropionic acid, 900 ml of toluene, and 2.9 g (0.04 mole) dimethylformamide. The phosgene cyclinder was turned on and 75 ml (1.05 moles) phosgene was allowed to accumulate in the funnel. The reactants were heated to 80° C. with stirring while the phosgene was added thereto. During the course of the phosgene addition, solids formed in the flask; however, ultimately they went into solution. After the phosgene addition, nitrogen was slowly added to the flask. The reaction was stopped, and a vacuum pulled on the flask to boil off the excess phosgene. The flask was then placed under a nitrogen atmosphere. The solvent was stripped off, leaving 233.2 g of yellow solids, which were identified by suitable analytical techniques as being the subject compound.

Workup

  1. customA three-liter, round-bottom flask was obtained
  2. customfitted with an overhead stirrer
  3. customAlso it was fitted with an exit line to a nitrogen/vacuum source
  4. customThe exit line went to a condenser
  5. customInto this flask was placed
  6. additionwas added
  7. customformed in the flask
  8. additionwas slowly added to the flask

Sources & evidence

ORD record
ord-5dfa1eaec85546b18b271d9fa1cfca72
Source dataset
uspto-grants-1985_09
Patent number
US04540804

Reaction notes

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