Nitrogen → 3,N,N-trimethyl-4-(2-triphenylsilanylsulfanyl-ethyl)-benzamide

HRID 1754904Notes

Reaction equation

HRID 1754904 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH:13]=[CH2:14])[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].[C:15]1([Si:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[SH:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(N=NC(C#N)(C)C)(C#N)C.N#N>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][S:22][Si:21]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 947NitrogenHCID 6547AzobisisobutyronitrileHCID 621128TriphenylsilanethiolHCID 668162113,N,N-Trimethyl-4-vinylbenzamide

Product 1

HCID 866727583,N,N-trimethyl-4-(2-triphenylsilanylsulfanyl-ethyl)-benzamideYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,N,N-trimethyl-4-vinyl-benzamide (706 mg, 3.73 mmol), triphenylsilanethiol (1.76 g, 6.00 mmol) and AIBN (185 mg, 1.13 mmol) in toluene (16 ml) was heated with stirring at 88° C. for two hours in a sealed test tube in an N2 atmosphere. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give 3,N,N-trimethyl-4-(2-triphenylsilanylsulfanyl-ethyl)-benzamide (1.24 g, 69%).

Workup

  1. temperaturewas heated
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-886234ea72eb430e950773cdd21d10f0
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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