4-Methoxybenzenethiol → HCID 86647351, compound

HRID 2068000Notes

Reaction equation

HRID 2068000 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1.[C:12]([O:16][C:17](=[O:27])[NH:18][C:19]1[S:20][C:21]([F:26])=[C:22]([CH2:24]Cl)[N:23]=1)([CH3:15])([CH3:14])[CH3:13].[Cl-].[NH4+]>C1COCC1>[C:12]([O:16][C:17](=[O:27])[NH:18][C:19]1[S:20][C:21]([F:26])=[C:22]([CH2:24][S:11][C:8]2[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[N:23]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 127654-MethoxybenzenethiolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59570820HCID 59570820, compound2×

Product 1

HCID 86647351HCID 86647351, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Sodium hydride (60%, 58 mg, 1.44 mmol) was added to a solution of 4-methoxythiophenol (0.19 mL, 1.56 mmol) in THF (5 mL). The resulting slurry was treated with a solution of Intermediate 105: (4-chloromethyl-5-fluoro-thiazol-2-yl)-carbamic acid tert-butyl ester (320 mg, 1.2 mmol) in THF (2 mL). After one hour, sat. ammonium chloride was added (1 mL) and THF was removed at reduced pressure. The residue was partitioned with water (5 mL) and diethyl ether (2×10 mL). The organic layer was concentrated an purified by silica gel chromatography (EtOAc/hexane) to afford [5-fluoro-4-(4-methoxy-phenylsulfanylmethyl)-thiazol-2-yl]-carbamic acid tert-butyl ester as a colorless foam (285 mg, 64% yield).

Workup

  1. customwas removed at reduced pressure
  2. customThe residue was partitioned with water (5 mL) and diethyl ether (2×10 mL)
  3. concentrationThe organic layer was concentrated
  4. customan purified by silica gel chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-ea01db9c88fe4443a56f32c37fd2784c
Source dataset
uspto-grants-2012_10
Patent number
US08293919B2

Reaction notes

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