Acetic Acid → HCID 23195142, compound

HRID 970330Notes

Reaction equation

HRID 970330 reaction equation
ClCC([NH:5][C:6](C)(C)[CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=O.NC(N)=S.[C:20](O)(=O)[CH3:21]>CCO>[CH3:10][C:9]1[C:20]([CH3:21])=[N:5][CH:6]=[CH:7][C:8]=1[CH2:13][CH2:12][NH2:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2723790ThioureaHCID 59019555HCID 59019555, compound

Product 1

HCID 23195142HCID 23195142, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 260B (1.30 g, 5.75 mmol), thiourea (524 mg, 6.90 mmol), acetic acid (2 ml) and EtOH (10 ml) was refluxed overnight. The reaction mixture was cooled to room temperature and the solid that separated out was filtered. The filtrate was concentrated and made acidic using 1N HCl. The aqueous solution was washed with EtOAc (2×25 mL), cooled to 0° C. and basified with 2N NaOH. The sodium hydroxide layer was re-extracted with EtOAc (2×25 mL), washed with water (25 mL), dried over Na2SO4 and concentrated under reduced pressure to give 260C (390 mg, 45%) 1NMR (CDCl3) δ 8.45 (d, 2H), 7.06 (d, 2H), 2.58 (s, 2H), 1.06 (s, 6H)

Workup

  1. temperaturewas refluxed overnight
  2. customthe solid that separated out
  3. filtrationwas filtered
  4. concentrationThe filtrate was concentrated
  5. washThe aqueous solution was washed with EtOAc (2×25 mL)
  6. temperaturecooled to 0° C. and basified with 2N NaOH
  7. extractionThe sodium hydroxide layer was re-extracted with EtOAc (2×25 mL)
  8. washwashed with water (25 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-215b526a5df84c189d5f6a294674d865
Source dataset
uspto-grants-2007_12
Patent number
US07312209B2

Reaction notes

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