Ethyl bromoacetate → HCID 86708911, compound

HRID 1522062Notes

Reaction equation

HRID 1522062 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][CH2:10][NH:9][S:8]2(=[O:14])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CS(C)=O>[O:13]=[S:8]1(=[O:14])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][CH2:11][CH2:10][N:9]1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 713571562-Phenyl-1lambda~6~,2,6-thiadiazinane-1,1-dione

Product 1

HCID 86708911HCID 86708911, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 2-phenyl-1,2,6-thiadiazinan 1,1-dioxide (400 mg, 1.89 mmol) in DMSO (15 mL), were added K2CO3 (522.4 mg, 3.78 mmol) and ethyl bromoacetate (379.1 mg, 2.27 mmol). The reaction mixture was agitated for 4 hr and extracted with ethyl acetate and brine. The organic layer was dried over MgSO4 and the residue was purified by silica gel column chromatography to yield ethyl 2-(1,1-dioxido-6-phenyl-1,2,6-thiadiazinan-2-yl)acetate (468 mg, 1.56 mmol, 83%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.45-7.34 (m, 3H), 7.30-7.25 (m, 1H), 4.28-4.20 (q, J=7.1 Hz, 2H), 4.03 (s, 2H), 3.82-3.73 (m, 4H), 1.99-1.91 (m, 2H), 1.30 (t, J=7.1 Hz, 3H).

Workup

  1. extractionextracted with ethyl acetate and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-498df3de51cf4708bb7638b013d8b8e0
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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