Hydrochloric Acid → HCID 68087716, compound

HRID 1627398Notes

Reaction equation

HRID 1627398 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:27])([CH3:26])[C:12]([NH:14][NH:15][C:16](=[S:25])[NH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+].Cl>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:12]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:16](=[S:25])[NH:15][N:14]=2)([CH3:27])[CH3:26])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86662261HCID 86662261, compound

Product 1

HCID 68087716HCID 68087716, compoundYield 65%

Procedure

A mixture of 2-(2-(3,4-dimethoxyphenyl)-2-methylpropanoyl)-N-(4-fluorophenyl)-hydrazinecarbothioamide (1.23 g, 3.14 mmol) and 2N NaOH (25 mL) was refluxed overnight. The reaction mixture was cooled to room temperature and acidified with 3N HCl to pH 5. The aqueous solution was extracted with DCM (30 mL×2). The combined organic layers were dried over MgSO4, filtered, and evaporated. The residue was purified by flash chromatography to give the title compound (760 mg, 65%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 12.52 (s, 1H), 6.94-6.90 (m, 2H), 6.70 (d, 1H), 6.60-6.57 (m, 2H), 6.50-6.46 (m, 2H), 3.89 (s, 3H), 3.77 (s, 3H), 1.57 (s, 6H).

Workup

  1. temperaturewas refluxed overnight
  2. extractionThe aqueous solution was extracted with DCM (30 mL×2)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-235a66b4d9264979b7c86ff441b23220
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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