Dimethylformamide dimethyl acetal → HCID 20548512, compound

HRID 2058870Notes

Reaction equation

HRID 2058870 reaction equation
[CH3:1][CH:2]([CH2:19][CH3:20])[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:23](OC)[N:24]([CH3:26])[CH3:25].Cl.CN>>[CH3:23][N:24]1[CH:26]=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:15])[F:16])[CH:8]=2)[C:5](=[O:17])[C:4]([C:3](=[O:18])[CH:2]([CH3:1])[CH2:19][CH3:20])=[CH:25]1

Participants

4

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 6364545Methylamine hydrochlorideHCID 20548493HCID 20548493, compound

Product 1

HCID 20548512HCID 20548512, compound

Procedure

A 1.3 g. portion of impure 5-methyl-1-(3-trifluoromethylphenyl)-2,4-heptanedione was reacted with 50 ml. of N,N-dimethylformamide dimethyl acetal, and then with 2 g. of methylamine hydrochloride as described in Example 12. The impure product was purified as described in Example 12, except that the final product was subjected to an additional step of trituration under hexane to obtain 0.08 g. of the desired product, m.p. 109°-111°, showing the following nmr peaks in CDCl3 : δ7.3-8.1 (m, 6H, aromatic); 3.9-4.2 (m, 1H, COCH); 3.8 (s, 3H, N--CH3); 1.2-2.0 (m, 2H, CH2CH3); 1.1-1.2 (d, 3H, CHCH3); 0.8-1.1 (t, 3H, CH2CH3).

Workup

  1. customThe impure product was purified
  2. customto obtain 0.08 g

Sources & evidence

ORD record
ord-ec129bec16d74d208129d7a249f45d73
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

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