Phenethyl bromide → HCID 70675144, compound

HRID 1522060Notes

Reaction equation

HRID 1522060 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][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=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][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[S:16]1(=[O:22])=[O:21])[CH2:9]2

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 86708909HCID 86708909, compound

Product 1

HCID 70675144HCID 70675144, compoundYield 13.7%

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 (2-bromoethyl)benzene (50 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-(1,1-dioxido-6-phenethyl-1,2,6-thiadiazinan-2-yl)acetamide (8 mg, 13%, white solid). 1H NMR (300 MHz, DMSO-d6): δ 7.33-7.19 (m, 5H), 7.01-6.98 (brd, 1H), 4.06-4.047 (m, 1H), 3.71 (s, 2H), 3.53-3.49 (m, 2H), 3.38-3.33 (m, 4H), 2.94-2.87 (m, 2H), 1.92-1.60 (m, 14H).

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-ff29715dfbe64719be253951398f9f28
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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