Phosgene → HCID 20304283, compound

HRID 237055Notes

Reaction equation

HRID 237055 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6](=[O:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9].C(N(CC)CC)C.[C:25](Cl)(Cl)=[O:26]>O1CCCC1>[F:13][C:7]([F:12])([C:8]([F:9])([F:10])[F:11])[C:6]([NH:5][C:4]1[CH:3]=[C:2]([N:1]=[C:25]=[O:26])[CH:17]=[CH:16][CH:15]=1)=[O:14]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 53939566HCID 53939566, compound

Product 1

HCID 20304283HCID 20304283, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-5 °C

Procedure

Sixty-three and one half grams of m-amino pentafluoropropionanilide is dissolved in 150 ml of tetrahydrofuran containing 65 g. of triethylamine. This mixture is added dropwise with cooling to 37 g. of phosgene dissolved in 150 ml of tetrahydrofuran cooled to -5° C. When addition is complete the mixture is allowed to warm up to room temperature. The triethylamine hydrochloride is filtered off and the solvent is removed under vacuum. The product, 70 g., was not isolated but diluted to 140 ml with tetrahydrofuran and used in subsequent reactions.

Workup

  1. additionThis mixture is added dropwise
  2. temperaturewith cooling to 37 g
  3. additionWhen addition
  4. temperatureto warm up to room temperature
  5. filtrationThe triethylamine hydrochloride is filtered off
  6. customthe solvent is removed under vacuum
  7. custom, was not isolated

Sources & evidence

ORD record
ord-54a8eb436e4b455c86cfc13c93cfd17d
Source dataset
uspto-grants-1979_06
Patent number
US04159344

Reaction notes

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