Acetamide → 1,3,5-Triazine-2-carbonitrile, 4,6-dimethoxy-

HRID 2413076Notes

Reaction equation

HRID 2413076 reaction equation
[C-]#N.[K+].[C:4]([NH2:7])(=O)C.[Cl-].C[N+](C)(C)[C:11]1[N:16]=[C:15]([O:17][CH3:18])[N:14]=[C:13]([O:19][CH3:20])[N:12]=1>O>[C:4]([C:11]1[N:12]=[C:13]([O:19][CH3:20])[N:14]=[C:15]([O:17][CH3:18])[N:16]=1)#[N:7]

Participants

5

Reactant 3

HCID 178AcetamideHCID 9032Potassium CyanideHCID 131413314,6-Dimethoxy-N,N,N-trimethyl-1,3,5-triazin-2-aminium chloride

Product 1

HCID 23202681,3,5-Triazine-2-carbonitrile, 4,6-dimethoxy-Yield 38.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 26 g of potassium cyanide and 60 g of oven-dried acetamide was heated to 85°-90° C. To this melt was added 24 g of the product from Example 2 in portions over a period of 15-20 minutes. The resulting brown reaction solution was heated to 90°-100° C. for an additional one hour. When the solution had cooled to room temperature, water was added and the aqueous layer was extracted with ether and methylene chloride. The combined organic extracts were backwashed with several small portions of water, brine, and were then dried over magnesium sulfate and concentrated in vacuo to afford 6.5 g of 2-cyano-4,6-dimethoxy-1,3,5-triazine as a light yellow solid.

Workup

  1. temperaturewas heated to 85°-90° C
  2. temperatureThe resulting brown reaction solution was heated to 90°-100° C. for an additional one hour
  3. extractionthe aqueous layer was extracted with ether and methylene chloride
  4. dry with materialwere then dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-232248879c4f4b3d86c8de105672fe7c
Source dataset
uspto-grants-1985_01
Patent number
US04496392

Reaction notes

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