Triethylamine → HCID 90418366, compound

HRID 2177206Notes

Reaction equation

HRID 2177206 reaction equation
[F:1][C:2]([C:5]1[S:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)[C:6]=1[CH2:18][OH:19])([F:4])[CH3:3].[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>ClCCl>[CH3:20][S:21]([O:19][CH2:18][C:6]1[C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=[N:8][S:9][C:5]=1[C:2]([F:4])([F:1])[CH3:3])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90418631HCID 90418631, compound

Product 1

HCID 90418366HCID 90418366, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
28 °C

Procedure

Into a 25-mL round-bottom flask, was placed [5-(1,1-difluoroethyl)-3-(4-ethylphenyl)-1,2-thiazol-4-yl]methanol (32 mg, 0.11 mmol, 1.00 equiv), dichloromethane (2 mL), MsCl (0.0258 g), triethylamine (34.2 mg, 0.34 mmol, 2.99 equiv). The resulting solution was stirred for 0.5 h at 28° C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of 10 mL of water, the organic phase was collected. 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 0.061 g (crude) of [5-(1,1-difluoroethyl)-3-(4-ethylphenyl)-1,2-thiazol-4-yl]methyl methanesulfonate as yellow oil. Mass spectrum (ESI, m/z): Calcd. for C15H17F2NO3S2, 362.4 (M+H). found 362.4.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 10 mL of water
  3. customthe organic phase was collected
  4. extractionThe aqueous phase was extracted with 3×10 mL of dichloromethane
  5. washThe resulting mixture was washed with 2×20 mL of sodium chloride
  6. dry with materialThe mixture was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 0.061 g (crude) of [5-(1,1-difluoroethyl)-3-(4-ethylphenyl)-1,2-thiazol-4-yl]methyl methanesulfonate as yellow oil

Sources & evidence

ORD record
ord-17699341e6a7433281533faa1859ba6d
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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