Ethyl iodoacetate → Ethyl 2-(2,4-dioxo-4H-thieno[3,2-d][1,3]oxazin-1-yl)acetate

HRID 2374739Notes

Reaction equation

HRID 2374739 reaction equation
[H-].[Na+].[NH:3]1[C:8]2[CH:9]=[CH:10][S:11][C:7]=2[C:6](=[O:12])[O:5][C:4]1=[O:13].I[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C)C=O>[O:13]=[C:4]1[N:3]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2[CH:9]=[CH:10][S:11][C:7]=2[C:6](=[O:12])[O:5]1

Participants

5

Reactant 3

HCID 12183Ethyl iodoacetateHCID 24758Sodium hydrideHCID 27775521H,2H,4H-thieno(3,2-d)(1,3)oxazine-2,4-dione

Product 1

HCID 10106395Ethyl 2-(2,4-dioxo-4H-thieno[3,2-d][1,3]oxazin-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (851 mg, 60% dispersion in oil) in dry N,N-dimethylformamide (DMF) (15 ml) was cooled under argon in an ice bath. A solution of 1H-thieno[3,2-d][1,3]oxazine-2,4-dione (3 g) in DMF (10 ml) was added over ca 20 min. The reaction mixture was stirred for 30 min at room temperature, then recooled in an ice bath. Ethyl iodoacetate (4.55 g) was added and the mixture stirred at room temperature for ca 2 h. The solution was concentrated to about half volume and cooled in an ice bath. Water was added (ca 200 ml). After 10 min the precipitate was filtered off and washed with water and hexane and dried at 40° C. in vacuo overnight. The title compound was obtained as a white solid (3.62 g, 80%). 1H-NMR (CDCl3) δ 1.30 (3H, t), 4.28 (2H, q), 4.71 (2H, s), 6.77 (1H, d), 7.87 (1H, d). (APCI+) Found (M+1)=256, C10H9NO5S requires 255.

Workup

  1. customrecooled in an ice bath
  2. stirringthe mixture stirred at room temperature for ca 2 h
  3. concentrationThe solution was concentrated to about half volume
  4. temperaturecooled in an ice bath
  5. additionWater was added (ca 200 ml)
  6. filtrationAfter 10 min the precipitate was filtered off
  7. washwashed with water and hexane
  8. customdried at 40° C. in vacuo overnight

Sources & evidence

ORD record
ord-390af917ac0b480ab93e20e74003a3cc
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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