Sodium hydride → 5-Dimethylthiocarbamoyloxy-benzofuran-2-carboxylic acid methyl ester

HRID 2215097Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:8]=2[CH:9]=1)=[O:4].[H-].[Na+].[CH3:17][N:18]([CH3:22])[C:19](Cl)=[S:20]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][C:19](=[S:20])[N:18]([CH3:22])[CH3:17])=[CH:10][C:8]=2[CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 5-hydroxy-benzofuran-2-carboxylic acid methyl ester (2 g, 10 mmol) in 50 mL dry DMF was treated portionwise with NaH (252 mg of a 95% dispersion in mineral oil, 10 mmol). After 30 min, dimethylthiocarbamoyl chloride (1.9 g, 15 mmol) was added and the reaction stirred at 40° C. for 1.5 hours. The reaction mixture was then concentrated in vacuo, and the residue taken up in EtOAc. The organic layer was then washed 1×water, 1×brine, dried (Na2SO4) and the solvent removed in vacuo to give 3.5 g of the crude title compound. Recrystallization from CHCl3/hexanes, gave 1.3 g (45%) of the title compound. 400 MHz 1H NMR (DMSO-d6) δ 7.72 (s, 1H), 7.68 (d, 1H, J=9.8 Hz), 7.43 (s, 1H), 7.17 (d, 1H,J=9.8 Hz), 3.85 (s, 3H), 3.32 (s, 3H), 3.29 (s, 3H).

Workup

concentrationThe reaction mixture was then concentrated in vacuo
washThe organic layer was then washed 1×water, 1×brine
dry with materialdried (Na2SO4)
customthe solvent removed in vacuo
customto give 3.5 g of the crude title compound
customRecrystallization from CHCl3/hexanes

Sources & evidence

ORD record: ord-09dedb23ad394318956e1e15621a163a
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109222B2

Reaction notes

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