Dimethylcarbamoyl Chloride → HCID 90204876, compound

HRID 1480197Notes

Reaction equation

HRID 1480197 reaction equation
[F:1][C:2]1([C:6]2[CH:7]=[N+:8]([O-])[CH:9]=[CH:10][C:11]=2[O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH2:5][CH2:4][CH2:3]1.C[Si](C)(C)[C:21]#[N:22].CN(C)C(Cl)=O>ClCCl>[F:1][C:2]1([C:6]2[C:11]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]([C:21]#[N:22])=[N:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 90214903HCID 90214903, compound

Product 1

HCID 90204876HCID 90204876, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1-fluorocyclobutyl)-1-oxido-4-(2,2,2-trifluoroethoxy)pyridin-1-ium (example 127b, 1.65 g, 6.22 mmol) in dichloromethane (25 ml) was added trimethylsilanecarbonitrile (945 mg, 1.19 ml, 9.33 mmol) and dimethylcarbamic chloride (833 μl, 8.71 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into a separation funnel and extracted with a 1M 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/ethyl acetate gradient to yield the title compound (760 mg, 44%); MS (ESI, m/z): 275.5 (M+H+).

Workup

  1. additionThe reaction mixture was poured into a separation funnel
  2. extractionextracted with a 1M aqueous solution of sodium bicarbonate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated down to dryness
  5. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-50a6881c537549448704dfb97da9f5bd
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

Loading…