Triethylamine → 4-(3-Benzyloxy-propyl)-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole

HRID 2263376Notes

Reaction equation

HRID 2263376 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[S:15][C:16]=1[CH2:17]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS([Cl:40])(=O)=O>ClCCl.O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[S:15][C:16]=1[CH2:17][Cl:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59296181[4-(3-Benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol

Product 1

HCID 595946804-(3-Benzyloxy-propyl)-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.5 g of [4-(3-benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol in 15 mL of dichloromethane was added 1.026 mL of triethylamine and 0.484 mL of methanesulfonyl chloride. The resulting mixture was stirred at room temperature for 2 h. The mixture was then diluted with dichloromethane and water was added. The aqueous layer was separated and extracted three times with dichloromethane. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (heptane 90/ethyl acetate 10) to give 0.84 g of 4-(3-benzyloxy-propyl)-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole as a yellow oil.

Workup

  1. additionwas added
  2. customThe aqueous layer was separated
  3. extractionextracted three times with dichloromethane
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel (heptane 90/ethyl acetate 10)

Sources & evidence

ORD record
ord-08b1bc57f19e43398d00733223f932e4
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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