Thionyl Chloride → HCID 14067389, compound

HRID 614525Notes

Reaction equation

HRID 614525 reaction equation
[CH:1]1[N:9]2[C:4]([CH2:5][O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)=[N:3][C:2]=1[C:14]([OH:16])=O.S(Cl)([Cl:19])=O>>[CH:1]1[N:9]2[C:4]([CH2:5][O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)=[N:3][C:2]=1[C:14]([Cl:19])=[O:16]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12909281HCID 12909281, compound

Product 1

HCID 14067389HCID 14067389, compoundYield 83%

Procedure

5 g (0.023 mole) of 4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylic acid were suspended in 15 ml of thionyl chloride and the mixture obtained was refluxed for two hours during which time the solid material completely dissolved. Excess thionyl chloride was removed by azeotroping with benzene on a rotary evaporator and the product was triturated with ether, filtered off and dried to obtain 4.5 g (83% yield of 4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carbonyl chloride with a melting point of 240° C. (decomp).

Workup

  1. customthe mixture obtained
  2. temperaturewas refluxed for two hours during which time the solid material
  3. dissolutioncompletely dissolved
  4. customExcess thionyl chloride was removed
  5. customby azeotroping with benzene on a rotary evaporator
  6. customthe product was triturated with ether
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-de8aacaa292e44b69b6f78b94c6a08d3
Source dataset
uspto-grants-1979_03
Patent number
US04145419

Reaction notes

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