Triethylamine → HCID 59457456, compound

HRID 1710766Notes

Reaction equation

HRID 1710766 reaction equation
[Cl:1][C:2]1[O:3][CH:4]=[C:5]([CH2:7][OH:8])[N:6]=1.[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[CH3:9][S:10]([O:8][CH2:7][C:5]1[N:6]=[C:2]([Cl:1])[O:3][CH:4]=1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 11378512(2-CHLOROOXAZOL-4-YL)METHANOL

Product 1

HCID 59457456HCID 59457456, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-chloro-1,3-oxazol-4-yl)methanol (5 g, 37.44 mmol, 1 eq, prepared according to the method described in Tetrahedron Lett. (2004), 45, 3797-3802) in dichloromethane (250 ml) is reacted with methanesulfonyl chloride (3.19 ml, 41.19 mmol, 1.1 eq) in the presence of triethylamine (5.79 ml, 41.19 mmol, 1.1 eq) at 0° C. After 1 h 30, the mixture is poured into a saturated solution of ammonium chloride and extracted twice with dichloromethane. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum to afford 7.9 g of (2-chloro-1,3-oxazol-4-yl)methyl methanesulfonate i59. This product is used in the next step without further purification or analysis.

Workup

  1. extractionextracted twice with dichloromethane
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-65ec77fffeb0425fbc48b518f79e7c44
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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