Water → 6-amino-4-propargyl-2H-1,4-benzoxazin-3(4H)-one

HRID 1638835Notes

Reaction equation

HRID 1638835 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[NH:9][C:8]=2[CH:14]=1.[CH2:15](Cl)[C:16]#[CH:17].O>CN(C)C=O>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[N:9]([CH2:17][C:16]#[CH:15])[C:8]=2[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 122213-Chloro-1-propyneHCID 24758Sodium hydrideHCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 136490056-amino-4-propargyl-2H-1,4-benzoxazin-3(4H)-oneYield 58.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.08 g) was suspended in dry N,N-dimethylformamide (3 ml), and the suspension was cooled to 0° C. While stirring, 6-amino-2H-1,4-benzoxazin-3(4H)-one (0.5 g) was portionwise added to the suspension at 0° C., and the resultant mixture was stirred at the same temperature for 30 minutes. To the mixture, propargyl chloride (0.25 g) was dropwise added, and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with water, dried and concentrated to give 6-amino-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (0.36 g). m.p., 260.1° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 6 hours
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d18ba8cb7ccd4a3eb835443923322f02
Source dataset
uspto-grants-1989_11
Patent number
US04880925

Reaction notes

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