HCID 131711786, compound → HCID 14067395, compound

HRID 1706367Notes

Reaction equation

HRID 1706367 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]=[C:8]3[N:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:13](C(O)=O)[N:7]3[C:6]=2[CH:21]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8]3=[N:11][C:12]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][N:7]3[C:6]=2[CH:21]=1

Participants

3

Reactant 1

HCID 131711786HCID 131711786, compound

Product 1

HCID 14067395HCID 14067395, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

5.4 g (17.5 mmol) of the 4H-8-chloro-2-methoxycarbonyl-imidazo-[2,1-c][1,4]-benzoxazine-1-carboxylic acid prepared in Step E were stirred in 50 ml of Dowtherm A on an oil bath. The solution obtained bubbled vigorously when the oil bath reached 185°-195° C. When the effervescence had ceased, the solution was cooled and diluted with ether. The product crystallized out and was filtered off, washed well with ether and dried under vacuum over P2O5 to obtain 4.4 g (95% yield) of methyl 8-chloro-4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylate with a melting point of 239°-40° C. in the form of off-white needles.

Workup

  1. customThe solution obtained
  2. custombubbled vigorously when the oil bath
  3. customreached 185°-195° C
  4. temperaturethe solution was cooled
  5. additiondiluted with ether
  6. customThe product crystallized out
  7. filtrationwas filtered off
  8. washwashed well with ether
  9. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-c3bb00a3ddbe46e8b29b45c84a411e7f
Source dataset
uspto-grants-1980_06
Patent number
US04207318

Reaction notes

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