Dimethylcarbamoyl Chloride → HCID 71294391, compound

HRID 1747558Notes

Reaction equation

HRID 1747558 reaction equation
[F:1][C:2]([F:38])([F:37])[CH:3]([C:30]1[CH:35]=[CH:34][N+:33]([O-])=[CH:32][CH:31]=1)[O:4][C:5]1[C:14]([N:15]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[S:16]([CH2:19][CH2:20][CH3:21])(=[O:18])=[O:17])=[N:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1.C[Si]([C:43]#[N:44])(C)C.CN(C)C(Cl)=O.C(=O)(O)[O-].[Na+]>ClCCl.O>[C:43]([C:34]1[CH:35]=[C:30]([CH:3]([O:4][C:5]2[C:14]([N:15]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[S:16]([CH2:19][CH2:20][CH3:21])(=[O:18])=[O:17])=[N:13][C:12]3[C:7]([N:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:2]([F:38])([F:37])[F:1])[CH:31]=[CH:32][N:33]=1)#[N:44]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 86678206HCID 86678206, compound

Product 1

HCID 71294391HCID 71294391, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Compound B4 (210 mg, 0.367 mmol) obtained in Step 1 was dissolved in dichloromethane (4 mL). To the solution were added trimethylsilyl cyanide (0.25 mL, 1.8 mmol) and dimethylcarbamoyl chloride (0.17 mL, 1.8 mmol), and the mixture was refluxed for 24 hours. A saturated aqueous sodium bicarbonate solution and water were added to the reaction mixture. Extraction with ethyl acetate and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give Compound B5 (218 mg, 100% yield).

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. extractionExtraction with ethyl acetate
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-7ad68d4468d7488abc6c968d483dca0a
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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