Water → HCID 12282508, compound

HRID 2254051Notes

Reaction equation

HRID 2254051 reaction equation
O1CCOCC1.O.Cl.[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH2:14])[CH3:10].[Cl:16][C:17]1[CH:18]=[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]=[CH:18][C:17]([Cl: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 784805-Chloroisatoic anhydrideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 12282508HCID 12282508, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into a mixed liquor of 160 ml of dioxane with 40 ml of water were dissolved 10.5 g of glycine ethyl ester hydrochloride, and 11.9 g of 6-chloro-2H-3,1-benzoxazine-2,4(1H)-dione were added. To this were added dropwise 8.1 g of triethylamine at room temperature under stirring, and the mixture was stirred for 30 minutes. After stirring further for 1 hour, dioxane was distilled off and 100 ml of water were added. The deposits were collected by filtration, washed with water and dried. Then, these were recrystallized from carbon tetrachloride to obtain 11.0 g of title compound, m.p. 108°-110° C.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for 30 minutes
  3. stirringAfter stirring further for 1 hour
  4. distillationdioxane was distilled off
  5. addition100 ml of water were added
  6. filtrationThe deposits were collected by filtration
  7. washwashed with water
  8. customdried
  9. customThen, these were recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-3b5906912fba4e1897b8d497cf52fb2f
Source dataset
uspto-grants-1993_08
Patent number
US05234928

Reaction notes

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