Pyridine → HCID 20139137, compound

HRID 978356Notes

Reaction equation

HRID 978356 reaction equation
N[C:2]1[CH:15]=[CH:14][C:5]2[C:6](=[O:13])[O:7][C:8]([O:10][CH2:11][CH3:12])=[N:9][C:4]=2[CH:3]=1.[N:16]1C=CC=CC=1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>ClCCl>[C:23]([NH:16][C:15]1[CH:2]=[CH:3][C:4]2[N:9]=[C:8]([O:10][CH2:11][CH3:12])[O:7][C:6](=[O:13])[C:5]=2[CH:14]=1)([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 13827094HCID 13827094, compound

Product 1

HCID 20139137HCID 20139137, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-amino-2-ethoxy-4H-3,1-benzoxazin-4-one (0.2 m mol., 41 mg) and dry pyridine (0.1 ml) in dry dichloromethane (4 ml) at room temperature under anhydrous conditions was added ethyl chloroformate (0.05 ml, 0.52 m mol.) in one portion. After stirring for one hour, the reaction mixture was diluted with dichloromethane (16 ml), washed successively with water (15 ml), 5% CuSO4) and evaporated to dryness. The residue was stirred in anhydrous ether (2 ml) and filtered to afford 53 mg (95%) of the title compound, 7-carboethoxyamino-2-ethoxy-4H-3,1-benzoxazin-4-one as a colorless powder; m.p. 191°-193° C.; IR (KBr): νmax 3310 cm-1 (NH), 1735 cm-1 (ester, carbamyl); 1640 cm-1 (C=N); H'NMR (CDCl3): δ1.34 ppm (t, J=7.1 Hz, 3H, CH3CH2OCON), 1.44 ppm (t, J=7.1 Hz, 3H, CH)

Workup

  1. washwashed successively with water (15 ml), 5% CuSO4) and
  2. customevaporated to dryness
  3. stirringThe residue was stirred in anhydrous ether (2 ml)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ecbf52c7291441d0ac5754097ee14605
Source dataset
uspto-grants-1987_05
Patent number
US04665070

Reaction notes

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