Iodoethane → HCID 71580292, compound

HRID 1499993Notes

Reaction equation

HRID 1499993 reaction equation
[CH3:1][C:2]1[C:16]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[N:11]([CH3:12])[N:10]=[N:9][N:8]=1)=[O:5].I[CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:26]([N:6]([C:7]1[N:11]([CH3:12])[N:10]=[N:9][N:8]=1)[C:4](=[O:5])[C:3]1[CH:13]=[CH:14][C:15]([C:21]([F:24])([F:22])[F:23])=[C:16]([S:17]([CH3:20])(=[O:19])=[O:18])[C:2]=1[CH3:1])[CH3:27]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 60202789HCID 60202789, compound

Product 1

HCID 71580292HCID 71580292, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

100 mg (0.275 mmol) of 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and 43 mg (0.275 mmol) of iodoethane are dissolved in 5 ml of N,N-dimethylformamide, and 0.038 mg (0.275 mmol) of potassium carbonate is added. The reaction mixture is stirred at 80° C. for 16 h and taken up in 5 ml of water and extracted twice with 10 ml each time of dichloromethane. The organic phase is dried over Na2SO4 and concentrated. The residue is purified by means of preparative HPLC (acetonitrile, water). Yield 30 mg (26%).

Workup

  1. extractionextracted twice with 10 ml each time of dichloromethane
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by means of preparative HPLC (acetonitrile, water)

Sources & evidence

ORD record
ord-74066a69a8da4abeac10ba48952228f7
Source dataset
uspto-grants-2015_12
Patent number
US09204650B2

Reaction notes

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