Triethylamine → HCID 86677498, compound

HRID 1621175Notes

Reaction equation

HRID 1621175 reaction equation
[C:1]1([C:7]2[O:8][C:9]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[C:10]([CH2:12]O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.CS([Cl:31])(=O)=O>ClCCl>[Cl:31][CH2:12][C:10]1[N:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:8][C:9]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71279140HCID 71279140, compound

Product 1

HCID 86677498HCID 86677498, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-phenyl-5-(pyridin-3-yl)oxazol-4-yl)methanol (210 mg, 832 μmol) and triethylamine (253 mg, 348 μL, 2.5 mmol) in dichloromethane (4 mL) was added at 0-5° C. methanesulfonyl chloride (191 mg, 130 μL, 1.66 mmol). The ice bath was removed after 10 min and the reaction mixture was stirred at RT for 2 h. The reaction mixture was poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with water (1×25 mL) and brine (1×25 mL), dried over MgSO4 and concentrated in vacuo to give the product as light brown solid (197 mg, 728 μmol, 87.4%) which was used without further purification for the next step.

Workup

  1. customThe ice bath was removed after 10 min
  2. additionThe reaction mixture was poured into water (25 mL)
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layer was washed with water (1×25 mL) and brine (1×25 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f38f385b389542ba9efc37e76bb190ac
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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