Triethylamine → HCID 90418228, compound

HRID 2177209Notes

Reaction equation

HRID 2177209 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH2:14][OH:15])=[C:12]([C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2].[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C>ClCCl>[CH3:23][S:24]([O:15][CH2:14][C:13]1[C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=2)=[N:10][S:11][C:12]=1[C:16]([F:22])([F:21])[C:17]([F:18])([F:19])[F:20])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90418883HCID 90418883, compound

Product 1

HCID 90418228HCID 90418228, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Into a 100-mL round-bottom flask, was placed [3-(4-ethylphenyl)-5-(pentafluoroethyl)-1,2-thiazol-4-yl]methanol (108 mg, 0.32 mmol, 1.00 equiv), dichloromethane (10 mL). The solution was cooled to 0 degree C. MsCl (73 mg, 0.64 mmol, 2.00 equiv) and triethylamine (0.097 g, 0.96 mmol, 3.00 equiv) were added dropwise. The resulting solution was stirred for 2 h at 25° C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of 5 mL of water. Organic phase was separated and the aqueous phase was extracted with 3×10 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 2×20 mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.150 g (crude) of [3-(4-ethylphenyl)-5-(pentafluoroethyl)-1,2-thiazol-4-yl]methyl methanesulfonate as a white solid. And it could been used for the next step directly. Mass spectrum (ESI, m/z): Calcd. for C15H14F5NO3S2, 416.4 (M+H). found 416.4.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. temperatureThe solution was cooled to 0 degree C
  3. customThe reaction was then quenched by the addition of 5 mL of water
  4. customOrganic phase was separated
  5. extractionthe aqueous phase was extracted with 3×10 mL of dichloromethane
  6. washThe resulting mixture was washed with 2×20 mL of sodium chloride
  7. dry with materialThe mixture was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThis resulted in 0.150 g (crude) of [3-(4-ethylphenyl)-5-(pentafluoroethyl)-1,2-thiazol-4-yl]methyl methanesulfonate as a white solid

Sources & evidence

ORD record
ord-279a85db1f78479281c4ad572f36daec
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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