Triethylamine → HCID 135890139, compound

HRID 539867Notes

Reaction equation

HRID 539867 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][CH2:21][CH3:22])=[C:6]([C:8]2[NH:13][C:12](=[O:14])[C:11]([Br:15])=[C:10]([CH:16]([CH3:18])[CH3:17])[N:9]=2)[CH:7]=1.[CH2:23]([N:25]=[C:26]=[S:27])[CH3:24].C(N(CC)CC)C>C(O)C>[CH:16]([C:10]1[N:9]=[C:8]([C:6]2[CH:7]=[C:2]([NH:1][C:26]([NH:25][CH2:23][CH3:24])=[S:27])[CH:3]=[CH:4][C:5]=2[O:19][CH2:20][CH2:21][CH3:22])[NH:13][C:12](=[O:14])[C:11]=1[Br:15])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10966Ethyl isothiocyanateHCID 136197376HCID 136197376, compound

Product 1

HCID 135890139HCID 135890139, compoundYield 681.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (4.0 g, 10 mmol) of example 34 was suspended in ethanol (10 ml), and added with ethyl isothiocyanate (0.9 g, 1.1 mmol) and triethylamine (1 mL). After refluxed for 3 h, the reaction mixture was concentrated to dryness. The resultant solid was washed with distilled water and recrystallized from ethyl acetate-petroleum ether to give the title compound (3.4 g, yield: 74%). 1H NMR (DMSO-d6) δ: 12.38 (1H, br), 9.41 (1H, br), 7.74 (1H, d), 7.54 (1H, dd), 7.15 (1H, d), 4.04 (2H, t), 3.46 (2H, m), 3.37 (1H, m), 1.75 (2H, m), 1.18 (6H, d), 1.11 (3H, t), 0.97 (3H, t).

Workup

  1. temperatureAfter refluxed for 3 h
  2. concentrationthe reaction mixture was concentrated to dryness
  3. washThe resultant solid was washed with distilled water
  4. customrecrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-5758d10f2ecc4863a90072e72997b50b
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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