Water → HCID 46846700, compound

HRID 2039657Notes

Reaction equation

HRID 2039657 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16](=[S:18])[NH2:17])=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].Br[CH2:25][C:26]([C:28]1[N:33]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:31]=[CH:30][CH:29]=1)=O.O>C(O)C>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2[S:18][CH:25]=[C:26]([C:28]3[N:33]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:31]=[CH:30][CH:29]=3)[N:17]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 16726661HCID 16726661, compoundHCID 58496319HCID 58496319, compound

Product 1

HCID 46846700HCID 46846700, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 4-methoxydibenzo[b,d]furan-1-carbothioamide (140 mg, 0.544 mmol) in ethanol (5 mL) was added sodium bicarbonate (60 mg, 0.714 mmol) and ethyl 6-(2-bromoacetyl)picolinate (150 mg, 0.551 mmol). The stirring was continued at room temperature for 20 hours. The reaction mixture was poured into the water (25 mL) and extracted with ethyl acetate (2×25 mL). The organic layer was dried over anhydrous sodium sulphate and filtered. The filtrate was evaporated at reduced pressure to give the product, which was purified by column chromatography by using a gradient of ethyl acetate in hexane (0-6%). Yield—28%; Rf 0.5 (Ethyl acetate:Hexane (3:7); HPLC (purity): 98.1%; 1H-NMR (CDCl3) δ: 1.48-1.57 (m, 3H), 4.14 (s, 3H), 4.50-4.55 (m, 2H), 7.07 (d, 1H), 7.49-7.53 (m, 1H), 7.65-7.69 (m, 2H), 7.94-7.98 (m, 1H), 8.09 (d, 1H), 8.42 (s, 1H), 8.47 (d, 1H), 8.73 (d, 1H); MS m/z: 431.1 (M+1).

Workup

  1. extractionextracted with ethyl acetate (2×25 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. customThe filtrate was evaporated at reduced pressure
  5. customto give the product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-004917b277b84b94ab03166b22f01f20
Source dataset
uspto-grants-2013_11
Patent number
US08580795B2

Reaction notes

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