Acetic Acid → HCID 178437797, compound

HRID 471512Notes

Reaction equation

HRID 471512 reaction equation
[CH3:1][C:2]1[C:3]([C:12](=O)[CH2:13][CH3:14])=[C:4]([NH:8][C:9]([NH2:11])=[O:10])[S:5][C:6]=1[CH3:7].[OH-].[Na+].CC(O)=O>CCO>[CH2:13]([C:12]1[C:3]2[C:2]([CH3:1])=[C:6]([CH3:7])[S:5][C:4]=2[NH:8][C:9](=[O:10])[N:11]=1)[CH3:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 57456922HCID 57456922, compound

Product 1

HCID 178437797HCID 178437797, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4,5-dimethyl-3-propionylthiophen-2-yl)urea (Example 51a) (15.4 mg, 0.068 mmol) in dry EtOH (10 mL) was added sodium hydroxide (8.4 mg, 0.20 mmol). The reaction mixture was then stirred at RT for 30 minutes under nitrogen. The reaction mixture was neutralized with 10% AcOH and then concentrated to dryness. The residue was purified by chromatography on silica gel (Gradient 0-10% MeOH in dichloromethane) to give the title compound (2.7 mg, 19%). 1H NMR (400 MHz, CDCl3) δ 1.42 (t, J=7.6 Hz, 3H), 2.31 (s, 3H), 2.33 (s, 3H), 3.06 (q, J=7.6 Hz, 2H). MS 209 (MH+).

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by chromatography on silica gel (Gradient 0-10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-6893214542664b818c7f1b760cbc9d75
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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