O-Cresol → HCID 18174720, compound

HRID 747428Notes

Reaction equation

HRID 747428 reaction equation
Cl[C:2]1[S:3][C:4]([CH2:14][CH2:15][CH2:16][OH:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH3:57][C:58]1[NH:59][CH:60]=[CH:61][N:62]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.O1CCCC1>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:59]3[CH:60]=[CH:61][N:62]=[C:58]3[CH3:57])[S:3][C:4]=2[CH2:14][CH2:15][CH2:16][O:17][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH3:18])=[CH:8][CH:9]=1

Participants

10

Reactant 6

HCID 335O-CresolHCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 18174758HCID 18174758, compound

Product 1

HCID 18174720HCID 18174720, compoundYield 14.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-chloro-4-(4-chlorophenyl)-5-thiazolepropanol (1.90 g), 2-methylphenol (1.30 g), tributylphosphine (2.43 g) and tetrahydrofuran (30 ml) was added 1,1′-(azodicarbonyl)dipiperidine (2.50 g) at room temperature, and the resulting mixture was stirred for 1 hour. After the reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography. The ethyl acetate-hexane (1:1, v/v)-eluted fraction was concentrated to give a yellow oil, which was dissolved in N,N-dimethylformamide (10 ml). 2-Methylimidazole (1.64 g) and potassium carbonate (2.76 g) were added to the reaction mixture, which was stirred at 120-130° C. for 4 hours. The reaction mixture was poured into water (100 ml), and the resulting solid precipitate was filtered, air-dried and recrystallized from acetone-hexane to give 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-[3-(2-methylphenoxy)propyl]thiazole as pale yellow prisms (394 mg, 14%). Melting point 112-113° C.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. concentrationThe ethyl acetate-hexane (1:1, v/v)-eluted fraction was concentrated
  3. customto give a yellow oil, which
  4. stirringwas stirred at 120-130° C. for 4 hours
  5. filtrationthe resulting solid precipitate was filtered
  6. customair-dried
  7. customrecrystallized from acetone-hexane

Sources & evidence

ORD record
ord-e77a1e5f943943f59f3c8921fd887e04
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Reaction notes

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