Benzyl Bromide → HCID 70675030, compound

HRID 1522059Notes

Reaction equation

HRID 1522059 reaction equation
Cl.[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH:12][C:13](=[O:23])[CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][NH:17][S:16]1(=[O:22])=[O:21])[CH2:9]2.C([O-])([O-])=O.[K+].[K+].Br[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH:12][C:13](=[O:23])[CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][N:17]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[S:16]1(=[O:22])=[O:21])[CH2:9]2

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86708909HCID 86708909, compound

Product 1

HCID 70675030HCID 70675030, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-(adamantan-2-yl)-2-(1,1-dioxido-1,2,6-thiadiazinan-2-yl)acetamide hydrochloride (50 mg, 0.135 mmol) in DMF (1 mL), were added K2CO3 (93.3 mg, 0.675 mmol) and (bromomethyl)benzene (46.2 mg, 0.27 mmol). The reaction mixture was agitated for 4 hr at room temperature 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 N-(adamantan-2-yl)-2-(6-benzyl-1,1-dioxido-1,2,6-thiadiazinan-2-yl)acetamide (53 mg, 94%, white solid). 1H NMR (300 MHz, DMSO-d6): δ 7.72-7.69 (brd, 1H), 7.39-7.28 (m, 5H), 4.17 (s, 2H), 3.86-3.83 (m, 1H), 3.79 (s, 2H), 3.46-3.42 (m, 2H), 3.17-3.14 (m, 2H), 1.93-1.89 (m, 2H), 1.80-1.67 (m, 12H), 1.52-1.48 (m, 2H).

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-21976568d1094e1091b75ebbe86bf161
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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