Potassium Hydroxide → (2-Amino-4,5-dimethylthiophen-3-yl)(phenyl)methanone

HRID 1744901Notes

Reaction equation

HRID 1744901 reaction equation
[C:1]([C:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[S:11][C:10]=1[NH:16]C(=O)C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>>[NH2:16][C:10]1[S:11][C:12]([CH3:15])=[C:13]([CH3:14])[C:9]=1[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:8]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 22225917HCID 22225917, compound

Product 1

HCID 615540(2-Amino-4,5-dimethylthiophen-3-yl)(phenyl)methanone

Procedure

General Method B. A solution of 12a (0.3 g, 1.1 mmole) in KOH (3.5 equivalents in methanol-water 1:1) was refluxed for 45 minutes, evaporated and taken up in dichloromethane. The solution was washed three times with water, dried and evaporated to a solid that was recrystallized from ethanol-water as yellow crystals. Yield 0.25 g, 100%. 1H NMR (CDCl3) δ: 1.5 (s, 3H, CH3), 2.1 (s, 3H, CH3), 6.4 (br s, 2H, NH2), 7.2–7.5 (m, 5H, C6H5). 13C NMR (CDCl3) δ: 12.5, 15.2, 114.9, 117.2, 127.8, 128.0, 128.8, 130.4, 141.7, 162.8, 193.0.

Workup

  1. customevaporated
  2. washThe solution was washed three times with water
  3. customdried
  4. customevaporated to a solid
  5. customthat was recrystallized from ethanol-water as yellow crystals

Sources & evidence

ORD record
ord-2f1ece7a0b5d416990f31b1fa453f0e6
Source dataset
uspto-grants-2006_03
Patent number
US07019027B2

Reaction notes

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