Triethylamine → HCID 178472768, compound

HRID 1746230Notes

Reaction equation

HRID 1746230 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:13])=[CH:5][C:6](=[O:12])[S:7]2.C(N(CC)CC)C.[CH2:21]([O:23][C:24](=[O:29])[CH2:25][N:26]=[C:27]=[O:28])[CH3:22]>C(Cl)Cl>[CH2:21]([O:23][C:24](=[O:29])[CH2:25][NH:26][C:27]([C:5]1[C:6](=[O:12])[S:7][C:8]2[C:3]([C:4]=1[OH:13])=[C:2]([F:1])[CH:11]=[CH:10][CH:9]=2)=[O:28])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76283Ethyl isocyanatoacetateHCID 178516560HCID 178516560, compound

Product 1

HCID 178472768HCID 178472768, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
120 °C

Procedure

5-Fluoro-4-hydroxy-thiochromen-2-one (500 mg, 2.55 mmol) was placed in a CEM Microwave vessel and suspended in anhydrous DCM (5 mL.) Triethylamine (710 uL, 5.1 mmol) and isocyanato-acetic acid ethyl ester (572 uL, 5.1 mmol) were added in one portion and the reaction heated to 120° C. in a CEM Discovery Microwave system. After three hours, the reaction was cooled diluted with 10 volumes of dichloromethane, washed with an equal volume of 1N HCl and dried over magnesium sulfate to provide the title compound which was used in the next step without further purification.

Workup

  1. additionwere added in one portion
  2. temperaturethe reaction was cooled
  3. washwashed with an equal volume of 1N HCl
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-08a01cc0ff114b21b3359ee4aac802b1
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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