Triethylamine → HCID 87233425, compound

HRID 1257989Notes

Reaction equation

HRID 1257989 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:24])=[C:7]([C:15]([C:17]2[CH:18]=[N:19][N:20]([CH3:23])[C:21]=2[OH:22])=[O:16])[CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])=[O:4].C(N(CC)CC)C.[CH3:32][CH2:33][S:34][C:35](Cl)=[O:36]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:24])=[C:7]([C:15]([C:17]2[CH:18]=[N:19][N:20]([CH3:23])[C:21]=2[O:22][C:35]([S:34][CH2:33][CH3:32])=[O:36])=[O:16])[CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18056Ethyl chlorothioformateHCID 178499013HCID 178499013, compound

Product 1

HCID 87233425HCID 87233425, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Hydroxy-1-methylpyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketone (290 mg, 0.82 mmol) was dissolved in dry tetrahydrofuran (15 mL), and triethylamine (166 mg, 1.64 mmol) was added thereto. A solution (4 mL) of 96% S-ethyl chlorothiolformate (107 mg) dissolved in dry tetrahydrofuran was added thereto little by little under cooling with ice water. The reaction mixture was stirred for 90 minutes while the reaction temperature was allowed to warm to room temperature. The reaction solution was poured into ice water, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4) to obtain the desired product as an amorphous solid (202 mg, 0.46 mmol) (yield: 56%).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-0186fb81150543658780f8d65569c6f2
Source dataset
uspto-grants-2013_06
Patent number
US08466088B2

Reaction notes

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