Water → Methyl 2-phenoxythiazole-4-carboxylate

HRID 594210Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.[O-:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na+].O.C1(C)C=CC=CC=1>CS(C)=O.[Cl-].[Na+].O>[O:11]([C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of commercially available methyl 2-bromothiazole-4-carboxylate (1.000 g; 4.50 mmol) and sodium phenoxide (627 mg; 5.40 mmol) in anh. DMSO (20 ml) was heated to 80° C., under nitrogen, for 17 h. A second addition of sodium phenoxide (314 mg; 2.70 mmol) was performed, and the resulting mixture was further heated at 80° C. for 1 h. After cooling to rt, water (50 ml), brine (10 ml), and toluene (20 ml) were added. The separated aq. layer was further extracted with toluene (2×20 ml). The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=50/1) afforded methyl 2-phenoxythiazole-4-carboxylate as a yellow oil. LC-MS (conditions A): tR=0.73 min.; [M+H]+: 236.06 g/mol.

Workup

temperaturethe resulting mixture was further heated at 80° C. for 1 h
temperatureAfter cooling to rt
extractionThe separated aq. layer was further extracted with toluene (2×20 ml)
washThe mixed organic layers were washed with brine
dry with materialdried over anh. MgSO4
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure
customPurification by FC (DCM/MeOH=50/1)

Sources & evidence

ORD record: ord-2c8e1c5e66844ec58efd2082ba207fd6
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242970B2

Reaction notes

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