Dimethylformamide → HCID 86693805, compound

HRID 1754882Notes

Reaction equation

HRID 1754882 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH3:10])[CH:8]=O.[CH3:11][C:12]1[CH:18]=[C:17]([C:19]#[C:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:16]([CH3:25])=[CH:15][C:13]=1[NH2:14]>C(Cl)Cl>[CH3:6][N:7]([CH3:10])[CH:8]=[N:14][C:13]1[CH:15]=[C:16]([CH3:25])[C:17]([C:19]#[C:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:18][C:12]=1[CH3:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 86693799HCID 86693799, compound2×

Product 1

HCID 86693805HCID 86693805, compoundYield 11.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Phosphorus oxychloride (182 mg) was added to a mixture of 5 ml of dichloromethane and 145 mg of N,N-dimethylformamide at 25° C. After the mixture was stirred at 25° C. for 1 hour, 1 ml of a methylene chloride solution containing 200 mg of the 2,5-dimethyl-4-(3,3-dimethyl-1-butynyl)aniline (Compound 4-25) produced in Production Example 2 was added dropwise thereto. The mixture was stirred at 25° C. for 2.5 hours, and the reaction solution was then poured into ice water. The pH was adjusted to 11 with an aqueous 1 N potassium hydroxide solution, and extraction was performed 3 time with dichloromethane. The organic layer was collected, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), thereby obtaining 30 mg of N,N-dimethyl-N′-[2,5-dimethyl-4-(3,3-dimethyl-1-butynyl)phenyl]formamidine (Compound 52).

Workup

  1. customproduced in Production Example 2
  2. additionwas added dropwise
  3. stirringThe mixture was stirred at 25° C. for 2.5 hours
  4. extractionThe pH was adjusted to 11 with an aqueous 1 N potassium hydroxide solution, and extraction
  5. customThe organic layer was collected
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b33dfad3560b41488a20ec84ae062ee5
Source dataset
uspto-grants-2015_10
Patent number
US09169276B2

Reaction notes

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