1,1'-Thiocarbonyldiimidazole → HCID 58085787, compound

HRID 249828Notes

Reaction equation

HRID 249828 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[C:10]([F:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:14](N1C=CN=C1)(N1C=CN=C1)=[S:15]>C1COCC1>[F:13][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]2[C:11]=1[O:12][C:14](=[S:15])[NH:1]2

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 58085876HCID 58085876, compound

Product 1

HCID 58085787HCID 58085787, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-amino-4-fluoro-3-hydroxybenzoate (1.5 g, 8.11 mmol) and 1,1′-thiocarbonyldiimidazole (1.46 g, 8.2 mmol) in THF (30 mL) was stirred at ambient temperature overnight, and at 50° C. for 6 h. The reaction mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. The residue was washed with ether (3×50 mL) and dried to afford methyl 7-fluoro-2-thioxo-2,3-dihydrobenzoxazole-4-carboxylate (1.3 g, 70%) as a yellow solid. 1H NMR (500 MHz, CDCl3) δ 7.82-7.78 (m, 1H), 6.40 (t, J=9.0 Hz, 1H), 4.00 (s, 3H); (ESI+) m/z 228 (M+H).

Workup

  1. waitat 50° C. for 6 h
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customthe solvent was removed under reduced pressure
  4. washThe residue was washed with ether (3×50 mL)
  5. customdried

Sources & evidence

ORD record
ord-7b49a702a9ce4406b496c8a1a6d1f692
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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