Triethylamine → HCID 57804306, compound

HRID 2103422Notes

Reaction equation

HRID 2103422 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)[O:5][C:6]=1[CH2:7][OH:8].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:15][C:11]1[CH:10]=[C:9]([C:4]2[O:5][C:6]([CH2:7][O:8][S:24]([CH3:23])(=[O:26])=[O:25])=[C:2]([CH3:1])[N:3]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57804317HCID 57804317, compound

Product 1

HCID 57804306HCID 57804306, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Cool (0° C.) a solution of [2-(3-methyl-phenyl)-4-methyl oxazol-5-yl]-methanol (Example 3, 756 mg, 4 mmol) in dichloromethane (16 mL) and add, sequentially, DMAP (51 mg, 0.4 mmol), triethylamine (552 μL, 4 mmol) and methanesulfonyl chloride (323 μL, 4.2 mmol). Stir the resulting solution for 5 min., remove the cooling bath and stir for 25 min. Dilute this solution with ether, wash with hydrochloric acid (5 mL, 2M), brine, dry over MgSO4 and concentrate to give the title compound (743 mg).

Workup

  1. additionadd
  2. customremove the cooling bath
  3. stirringstir for 25 min
  4. additionDilute this solution with ether
  5. washwash with hydrochloric acid (5 mL, 2M), brine
  6. dry with materialdry over MgSO4
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-c74f6922c80e40c3838e17f5344ccc7b
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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