Allyl bromide → HCID 22595722, compound

HRID 1760528Notes

Reaction equation

HRID 1760528 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][C:8]2[CH:10]=[C:11]([S:14][CH3:15])[CH:12]=[CH:13][C:7]=2[NH:6][S:5]1(=[O:17])=[O:16])[CH3:3].[H-].[Na+].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C)C=O.C(OCC)(=O)C>[CH3:3][CH:2]([N:4]1[CH2:9][C:8]2[CH:10]=[C:11]([S:14][CH3:15])[CH:12]=[CH:13][C:7]=2[N:6]([CH2:22][CH:21]=[CH2:20])[S:5]1(=[O:17])=[O:16])[CH3:1]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 22595747HCID 22595747, compound

Product 1

HCID 22595722HCID 22595722, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dihydro-3-(1-methylethyl)-6-methylthio-1H-2,1,3-benzothiadiazine-2,2-dioxide (10 g, 0.0367 mol) was added to a suspension of sodium hydride (1.61 g, 60% dispersion) in dry dimethylformamide (200 ml) at room temperature under a nitrogen atmosphere. The pale grey suspension was stirred for ten mins, and then allyl bromide (3.49 ml, 0.0404 mol) was added in one portion. The reaction mixture was stirred at 80° C. for 3 hr. The mixture was then concentrated in vacuo to yield a brown residue. The residue was dissolved in ethyl acetate (50 ml) and washed with water (2×50 ml). The organic layer was then dried (MgSO4) and concentrated in vacuo to afford 3,4-dihydro-3-(1-methylethyl)-6-methylthio-1-(prop-2-en-1-yl)-1H-2,1,3-benzothiadiazine-2,2-dioxide. δ (1H NMR, DMSO, ppm): 1.1 (6H, d), 2.5 (3H, s), 4.1 (1H, m), 4.5 (2H, d), 4.7 (2H, s), 5.3 (1H, dd), 5.4 (1H, dd), 6.0 (1H, m), 7.0 (1H, d), 7.3 (2H, m).

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for 3 hr
  2. concentrationThe mixture was then concentrated in vacuo
  3. customto yield a brown residue
  4. washwashed with water (2×50 ml)
  5. dry with materialThe organic layer was then dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee4fd237ce064ac7bc0e5c8bc57abc2a
Source dataset
uspto-grants-2005_01
Patent number
US06844338B2

Reaction notes

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