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Triethylamine → HCID 22998066, compound

HRID 1352981
Notes
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Reaction equation

HRID 1352981 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=3)[CH2:10][C:11](O)([C:13]([F:16])([F:15])[F:14])[N:12]=2)=[N:6][CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:18]3[CH:19]=[CH:20][C:21]([S:24][CH3:25])=[CH:22][CH:23]=3)[CH:10]=[C:11]([C:13]([F:15])([F:14])[F:16])[N:12]=2)=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 229980615-Methyl-2-[4-hydroxy-1-[4-(methylthio)phenyl]-4-(trifluoromethyl)-4.5-dihydro-1h-imidazol-2-yl]pyridine

Product 1

HCID 22998066HCID 22998066, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the dihydro-imidazole of step 3 (3. 95 g, 13.9 mmol) and p-toluenesulfonic acid monohydrate (785 mg, 4 mmol) in toluene (500 ml) was heated to reflux for 4–5 hours. The reaction mixture was cooled and 10 ml of triethylamine was added and the solvent removed-under reduced pressure. The crude mixture was purified by chromatography on silica gel using ethyl acetate to give the desired product which was used in the next reaction without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4–5 hours
  3. temperatureThe reaction mixture was cooled
  4. customThe crude mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a71dbd4174844b54b4f78bcac5fab459
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07220770B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes