Toluene → HCID 637989, compound

HRID 1184936Notes

Reaction equation

HRID 1184936 reaction equation
[N+](C1C=CC=CC=1S([N:13]1[CH:20]2[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:22][CH:14]1[CH2:15]3)[CH2:19]2)(=O)=O)([O-])=O.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C1(S)C=CC=CC=1>O.CO.C(#N)C>[CH:14]12[CH2:22][CH:18]3[CH2:17][CH:16]([CH2:21][CH:20]([CH2:19]3)[NH:13]1)[CH2:15]2

Participants

8

Reactant 4

HCID 1140TolueneHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 68636858HCID 68636858, compound

Product 1

HCID 637989HCID 637989, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 100 mg (0.311 mmol) of N-(2-nitrophenylsulfonyl)-2-azaadamantane, 51.6 mg (0.373 mmol) of potassium carbonate and 0.54 g of toluene were added, and after adjusting the temperature to 50° C., 0.039 mL (0.380 mmol) of thiophenol was added. After stirring for 5 hours, acetonitrile, methanol and water were added to obtain a uniform solution of 2-azaadamantane.

Workup

  1. customto 50° C.

Sources & evidence

ORD record
ord-b6dad6952ddb4091b86e1ba196eef9d6
Source dataset
uspto-grants-2014_03
Patent number
US08669367B2

Reaction notes

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