Triethylamine → HCID 178469803, compound

HRID 1913531Notes

Reaction equation

HRID 1913531 reaction equation
C[N:2]([CH3:12])[CH:3]=[C:4]([N+:10]#[C-:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.[O:14]([C@H:21]1[CH2:26][CH2:25][C@H](N)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(O)CCC>[O:14]([C@H:21]1[CH2:26][CH2:25][C@H:12]([N:2]2[CH:3]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:10]=[CH:11]2)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 54355309Ethyl 3-(dimethylamino)-2-isocyanoacrylateHCID 178479275HCID 178479275, compound

Product 1

HCID 178469803HCID 178469803, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

Ethyl 3-(dimethylamino)-2-isocyanoacrylate (0.70 g) and the compound (1.14 g) obtained in Step 2 of this Reference Example were dissolved in n-butanol (7.0 mL). Then, to the solution, triethylamine (0.70 mL) was added at room temperature, and the mixture was stirred at 150° C. for 3.25 hours. The reaction solution was concentrated and then purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=50/50-ethyl acetate) to obtain the title compound (0.28 g).

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=50/50-ethyl acetate)

Sources & evidence

ORD record
ord-0554a94d9efe4374a330243fff4ac9da
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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