Thionyl Chloride → HCID 13341934, compound

HRID 2286867Notes

Reaction equation

HRID 2286867 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([C:12]([NH2:14])=O)[CH:10]=[CH:11][C:6]=2[O:5][CH:4]([C:15]([Cl:18])([Cl:17])[Cl:16])[NH:3]1.S(Cl)(Cl)=O>>[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:14])[CH:10]=[CH:11][C:6]=2[O:5][CH:4]([C:15]([Cl:18])([Cl:16])[Cl:17])[NH:3]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 13341928HCID 13341928, compound

Product 1

HCID 13341934HCID 13341934, compound

Procedure

3,4-Dihydro-4-oxo-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazine-6-carboxamide (prepared as described in Example 10--1.0 g.) and thionyl chloride (20 ml.) were heated together under reflux for 1 hour, cooled to room temperature, and drowned into ice-water (200 ml.). After stirring for 1 hour, the white suspension so formed was filtered off, washed with water, dried at 60° C. and extracted with toluene (3×200 ml.). The toluene extracts were combined, and the solvent was evaporated to give 3,4-dihydro-4-oxo-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazine-6-carbonitrile, m.p. 212°-214° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. customthe white suspension so formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried at 60° C.
  6. extractionextracted with toluene (3×200 ml.)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c192b84fff7f4c9c8a21f778a7413df5
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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