Dimethylformamide dimethyl acetal → HCID 13201811, compound

HRID 2058868Notes

Reaction equation

HRID 2058868 reaction equation
[CH3:1][CH:2]([CH3:19])[C:3](=[O:18])[CH2:4][C:5](=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24].Cl.CN>CO>[C:3]([C:4]1[C:5](=[O:17])[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:15])[F:16])[CH:8]=2)=[CH:24][N:23]([CH3:25])[CH:22]=1)(=[O:18])[CH:2]([CH3:19])[CH3:1]

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 6364545Methylamine hydrochlorideHCID 132018065-Methyl-1-[3-(trifluoromethyl)phenyl]hexane-2,4-dione

Product 1

HCID 13201811HCID 13201811, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 0.6 g. portion of impure 5-methyl-1-(3-trifluoromethylphenyl)-2,4-hexanedione was reacted overnight at reflux temperature with N,N-dimethylformamide dimethyl acetal as described in the examples above to obtain 0.8 g. of a dark oil. The oil was dissolved in methanol and reacted with 2 g. of methylamine hydrochloride under reflux for 4 hours. The reaction mixture was evaporated under vacuum to obtain a yellow solid, which was purified as described in Example 10 to obtain 0.09 g. of the desired product, m.p. 104°-105°, showing the following peaks in nmr analysis in DMSOd6 : δ7.6-8.3 (m, 6H, aromatic): 3.7-4.2 (m, 1H, COCH); 3.8 (s, 3H, N--CH3); 1.0-1.2 (d, 6H, CH(CH3)2).

Workup

  1. customto obtain 0.8 g
  2. customreacted with 2 g
  3. customThe reaction mixture was evaporated under vacuum
  4. customto obtain a yellow solid, which
  5. customwas purified
  6. customto obtain 0.09 g

Sources & evidence

ORD record
ord-f88e145ac1f546bf9bf3b567f6390495
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

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