Oxalyl chloride → HCID 13353849, compound

HRID 1658481Notes

Reaction equation

HRID 1658481 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[C:7]([NH2:17])([C:13]([F:16])([F:15])[F:14])([C:9]([F:12])([F:11])[F:10])[Cl:8].[N-]=C=O>N1C=CC=CC=1>[Cl:8][C:7]([N:17]=[C:2]=[O:3])([C:9]([F:12])([F:11])[F:10])[C:13]([F:14])([F:15])[F:16]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 105034Isocyanate2×HCID 130019518HCID 130019518, compound

Product 1

HCID 13353849HCID 13353849, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 127 g (1 mole) of oxalyl chloride, 165 g (1 mole) of perfluoropropyliden-2-imine, and 5 ml of pyridine was heated in a 600 ml Hastelloy tube at 100° for 4 hrs, 105° for 4 hrs, and 200° for 4 hrs. The bomb was cooled and vented, and the contents were filtered to remove suspended solid. Distillation gave 102.3 g of a 25:75 mixture of (CF3)2CClNH2 and the isocyanate, bp 46.0°-46.5°, and 29.3 g of pure isocyanate as a colorless liquid: bp 50.5°-51.0°; 19F nmr (CCl3F) ε 78.0 (s); ir (liquid) 4.40 μ.

Workup

  1. temperaturewas heated in a 600 ml Hastelloy tube at 100° for 4 hrs, 105° for 4 hrs
  2. temperatureThe bomb was cooled
  3. filtrationthe contents were filtered
  4. customto remove
  5. distillationDistillation
  6. customgave

Sources & evidence

ORD record
ord-bbccf335d3754dd2a15fa8adb629f362
Source dataset
uspto-grants-1976_06
Patent number
US03965074

Reaction notes

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