Chloroacetyl chloride → (S)-2-chloro-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamide

HRID 1043535Notes

Reaction equation

HRID 1043535 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH:9]([NH2:13])[CH2:8][O:7]2)([O-:3])=[O:2].C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:21][CH2:22][C:23]([NH:13][C@@H:9]1[CH2:8][O:7][C:6]2=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][N:11]2[CH2:10]1)=[O:24]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 598406212-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-amine

Product 1

HCID 68207026(S)-2-chloro-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamideYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon protection, I-7-(S)-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine-6-amine (134 mg, 0.73 mmol) was dissolved in anhydrous DMF (2 mL), added triethylamine (0.3 mL, 2.18 mmol), added dropwise chloroacetyl chloride (0.082 mL, 1.09 mmol) at 0° C., stirred for 2 h at room temperature, added saturated sodium bicarbonate solution, extracted by ethyl acetate, followed by anhydrous sodium sulphate drying and suction filtration, spun dry solvents, separated by column chromatography to give 92 mg yellow viscous liquid, yield was 50%.

Workup

  1. extractionextracted by ethyl acetate
  2. filtrationfollowed by anhydrous sodium sulphate drying and suction filtration
  3. customseparated by column chromatography

Sources & evidence

ORD record
ord-759d236d1fb04006b6fba195e4017cd1
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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