Dimethylcarbamoyl Chloride → HCID 90204330, compound

HRID 1480168Notes

Reaction equation

HRID 1480168 reaction equation
[CH:1]1([C:5]2[CH:6]=[N+:7]([O-])[CH:8]=[CH:9][C:10]=2[O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:4][CH2:3][CH2:2]1.C[Si]([C:22]#[N:23])(C)C.CN(C)C(Cl)=O>ClCCl>[CH:1]1([C:5]2[C:10]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]([C:22]#[N:23])=[N:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 90203464HCID 90203464, compound

Product 1

HCID 90204330HCID 90204330, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-cyclobutyl-4-(2,2,2-trifluoroethoxy)pyridine 1-oxide (Example 108d, 3.5 g, 14.2 mmol) in dichloromethane (55 ml) under argon atmosphere was added trimethylsilylcyanide (1.83 g, 2.47 ml, 18.4 mmol) followed by addition of dimethylcarbamoyl chloride (CAN 79-44-7, 2.28 g, 1.95 ml, 21.2 mmol). The reaction mixture was then stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane and extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the title compound (2.95 g, 77%) as light yellow solid. MS (ESI, m/z): 257.5 (M+H+).

Workup

  1. extractionextracted with an 1.0M aqueous solution of sodium bicarbonate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated down to dryness
  4. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient

Sources & evidence

ORD record
ord-6f5e494ca08c4adc8430b131428123a2
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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