Ethyl bromoacetate → HCID 19026999, compound

HRID 1032924Notes

Reaction equation

HRID 1032924 reaction equation
[H-].[Na+].[CH2:3]([NH:5][CH:6]1[C:11]2[CH:12]=[CH:13][S:14][C:10]=2[S:9](=[O:16])(=[O:15])[NH:8][CH2:7]1)[CH3:4].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[CH2:22]([O:21][C:19]([CH2:18][N:8]1[CH2:7][CH:6]([NH:5][CH2:3][CH3:4])[C:11]2[CH:12]=[CH:13][S:14][C:10]=2[S:9]1(=[O:15])=[O:16])=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 19026998HCID 19026998, compound

Product 1

HCID 19026999HCID 19026999, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, sodium hydride (0.44 g of 60% suspension in mineral oil, 0.011 mol) was washed free of mineral oil with petroleum ether. A solution of 3,4-dihydro-4-ethylamino-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide (2.32 g, 0.01 mol) in dimethylformamide (10 ml) was added dropwise with stirring over 1/4 hr. Stirring was continued for another 1/2 hr in the cooling bath. Then ethyl bromoacetate (1.25 ml, 0.011 mol) was added and the mixture was stirred for 1/4 hr. with cooling and 1 3/4 hrs. at ambient temperature. The volatile components were removed under high vacuum. The oil-solid residue was extracted with ethyl acetate (2×25 ml). The combined extracts were washed with saturated NaCl, dried, filtered and concentrated in vacuo to a viscous yellow oil (2.75 g). Yield was 86%.

Workup

  1. stirringStirring
  2. stirringthe mixture was stirred for 1/4 hr
  3. temperaturewith cooling
  4. custom1 3/4 hrs
  5. customat ambient temperature
  6. customThe volatile components were removed under high vacuum
  7. extractionThe oil-solid residue was extracted with ethyl acetate (2×25 ml)
  8. washThe combined extracts were washed with saturated NaCl
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to a viscous yellow oil (2.75 g)

Sources & evidence

ORD record
ord-aec9d625ee7d422bb8c1569f881f114d
Source dataset
uspto-grants-1994_05
Patent number
US05308842

Reaction notes

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