Ethyl Acetate → Methyl 2-thiomorpholinobenzoxazole-4-carboxylate

HRID 249871Notes

Reaction equation

HRID 249871 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[NH:15]1[CH2:20][CH2:19][S:18][CH2:17][CH2:16]1.CCOC(C)=O>C1COCC1>[S:18]1[CH2:19][CH2:20][N:15]([C:2]2[O:3][C:4]3[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=3)[N:6]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67164ThiomorpholineHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

Product 1

HCID 66874243Methyl 2-thiomorpholinobenzoxazole-4-carboxylateYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-chlorobenzoxazole-4-carboxylate (1.0 g, 4.7 mmol) and thiomorpholine (1.4 mL, 14 mmol) in THF (20 mL) was stirred at ambient temperature for 1 h. Then, the reaction mixture was poured into EtOAc (100 mL) and washed with 1N HCl (20 mL), H2O (20 mL), brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (silica gel, 5 to 50% EtOAc in hexanes) gave methyl 2-thiomorpholinobenzoxazole-4-carboxylate (1.1 g, 84%) as a yellow solid. 1H NMR and MS consistent.

Workup

  1. washwashed with 1N HCl (20 mL), H2O (20 mL), brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification by chromatography (silica gel, 5 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0f7835b081d14f89bf22931c71b90445
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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