Water → HCID 54570731, compound

HRID 2254053Notes

Reaction equation

HRID 2254053 reaction equation
O1CCOCC1.O.Cl.[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH2:14])[CH3:10].[F:16][C:17]1[C:18]([F:29])=[CH:19][C:20]2[NH:25]C(=O)[O:23][C:22](=O)[C:21]=2[CH:28]=1>C(N(CC)CC)C>[NH2:25][C:20]1[CH:19]=[C:18]([F:29])[C:17]([F:16])=[CH:28][C:21]=1[C:22]([NH:14][CH2:13][C:12]([O:11][CH2:9][CH3:10])=[O:15])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 2723640Glycine ethyl ester, hydrochlorideHCID 109324446,7-Difluoroisatoic anhydride

Product 1

HCID 54570731HCID 54570731, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

Into a mixed liquor of 280 ml of dioxane with 70 ml of water were dissolved 19 g of glycine ethyl ester hydrochloride, and 21.7 g of 6,7-difluoro-2H-3,1-benzoxazine-2,4(1H)-dione were added and 14.7 g of triethylamine were added dropwise at room temperature under stirring. After stirring further for 30 minutes, the mixture was heated to 70° C. and stirred for 1,5 hours. Dioxane was distilled off, 150 ml of water were added, then the crystals deposited were collected by filtration, washed with water, and dried. They were recrystallized from ethyl acetate to obtain 20 g of title compound. m.p. 147° C.

Workup

  1. additionwere added
  2. stirringAfter stirring further for 30 minutes
  3. stirringstirred for 1,5 hours
  4. distillationDioxane was distilled off
  5. addition150 ml of water were added
  6. filtrationthe crystals deposited were collected by filtration
  7. washwashed with water
  8. customdried
  9. customThey were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5aa05dd1b1294ab4855c95f2c16f9e3d
Source dataset
uspto-grants-1993_08
Patent number
US05234928

Reaction notes

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