Dimethylformamide → HCID 9818644, compound

HRID 480442Notes

Reaction equation

HRID 480442 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[C:7]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)#[N:8].CN=[C:17]=[S:18].CI.[CH3:21][N:22]([CH3:25])[CH:23]=[O:24]>O>[CH3:21][N:22]1[C:23](=[O:24])[C:1]([C:2]2[CH:5]=[CH:7][CH:9]=[C:10]([CH3:11])[CH:3]=2)=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:8]=[C:25]1[S:18][CH3:17]

Participants

7

Reactant 5

HCID 6228Dimethylformamide3×HCID 6328Methyl iodideHCID 75064-CyanopyridineHCID 11167Methyl isothiocyanateHCID 23665647Potassium tert-butoxide

Product 1

HCID 9818644HCID 9818644, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of potassium t-butoxide (1M in t-butanol, 11, 1 mol) was added dropwise to a stirring solution of ethyl 3-methylphenyl acetate (178 g, 1 mol) in N,N-dimethylformamide (2 l). A solution of 4-cyanopyridine (104.11 g, 1 mol) in N,N-dimethylformamide (1 l) was pumped into the reaction mixture over a period of about 4.5 h. The mixture was then stirred at room temperature for 3 h, before the dropwise addition of a solution of methyl isothiocyanate (68.4 ml, 1 mol) in N,N-dimethylformamide (50 ml) over a period of 10 min. After stirring for 1 h at room temperature, the reaction mixture was cooled to 3∞ C. and methyl iodide (62.3 ml, 1 mol) was added dropwise over a period of 10 min. Stirring was continued at room temperature overnight. The mixture was cooled to 3∞ C. and water (4 l) was pumped into the reaction mixture over a period of 6 h. The precipitate was removed by filtration, washed with water and dried in a vacuum oven to give the title compound. MS (m/z): 324 (M+H)+; C18H17N3OS requir. 323.4.

Workup

  1. temperaturethe reaction mixture was cooled to 3∞ C
  2. stirringStirring
  3. waitwas continued at room temperature overnight
  4. temperatureThe mixture was cooled to 3∞ C
  5. customThe precipitate was removed by filtration
  6. washwashed with water
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-b708003c555b43d88594c542e447b698
Source dataset
uspto-grants-2003_11
Patent number
US06649604B2

Reaction notes

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