Diethylamine → HCID 20500909, compound

HRID 1447467Notes

Reaction equation

HRID 1447467 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Cl:6][C:7]([Cl:23])([Cl:22])[CH:8](Cl)[CH:9]([N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]>O1CCCC1>[Cl:6][C:7]([Cl:23])([Cl:22])[CH:8]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:9]([N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 12945122HCID 12945122, compound

Product 1

HCID 20500909HCID 20500909, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

14.6 g (0.2 mol) of diethylamine were slowly added dropwise to 33.4 g (0.1 mol) of 1,1,1,2-tetrachloro-3-(1,2,4-triazol-1-yl)-5,5-dimethyl-hexan-4-one (Example 3) in 150 ml of tetrahydrofuran at room temperature. The mixture was then subsequently stirred at 50°-60° C. for 3 hours. The diethylamine hydrochloride which had precipitated was filtered off and the filtrate was concentrated in vacuo. According to thin layer chromatography of the residue over silica gel 60 (Merck, particle size 0.063-0.200 mm) and with ether/hexane in the ratio 1:1 as the running agent, 1,1,1-trichloro-2-diethylamino-3-(1,2,4-triazol-1-yl)-5,5-dimethyl-hexan-4-one was obtained as the pure diastereomer of the A* form, as a yellow oil, in a yield of 8.9 g (24.1% of theory), and as the pure diastereomer of the B* form, of melting point 103°-110° C., in a yield of 6.4 g (19.4% of theory).

Workup

  1. customThe diethylamine hydrochloride which had precipitated
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e44b766b65c248cdafa405244c1ba963
Source dataset
uspto-grants-1982_02
Patent number
US04316932

Reaction notes

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