Dimethylformamide → HCID 20085211, compound

HRID 1608773Notes

Reaction equation

HRID 1608773 reaction equation
[CH2:1]([C:5]1([CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14])[CH2:2][CH2:3][CH3:4].CN(C)[CH:23]=[O:24].[CH3:26][C:27]([CH3:30])([O-])[CH3:28].[K+].CI>C(OCC)C.O>[CH3:23][O:24][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:5]([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)([CH:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4])[C:6]([O:7][C:27]([CH3:30])([CH3:28])[CH3:26])=[O:14]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 20085198HCID 20085198, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20085211HCID 20085211, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a clear solution of 3-butyl-3-[(1,2,4-triazol-1-yl)methyl]-2(3H)-benzofuranone (5.0 g, 0.0184 mole) and dimethyl formamide (20 mL) in a 300 mL round bottom flask, potassium t-butoxide (6.2 g, 0.0553 mole) was added and the reaction mixture stirred at room temperature for 5 minutes before adding methyl iodide (3.2 g, 0.0221 m). The reaction mixture was stirred with heating at 40° C. for 1 hour and 1.0 g of water was added. The stirring was continued for an additional 2 hours at 40° C., before adding 100 mL of water and 100 mL of ethyl ether for work up. The organic phase was isolated and dried over magnesium sulfate, evaporated by rotary evaporator to afford 4.0 g of oily concentrate (yield 61%), Example 69 of Table 1.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperaturewith heating at 40° C. for 1 hour
  3. waitThe stirring was continued for an additional 2 hours at 40° C.
  4. customThe organic phase was isolated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated by rotary evaporator
  7. customto afford 4.0 g
  8. concentrationof oily concentrate (yield 61%), Example 69 of Table 1

Sources & evidence

ORD record
ord-72687c0e3b8d4041a65f99fad6879d9e
Source dataset
uspto-grants-1995_03
Patent number
US05397768

Reaction notes

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