Sodium Hydroxide → HCID 57860960, compound

HRID 1928841Notes

Reaction equation

HRID 1928841 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:23][C@H:24]1[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25]1)[CH:17]=[CH:16]2)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>CO.O>[C@H:24]1([NH:23][C:18]2[CH:17]=[CH:16][C:15]3[C:20](=[CH:21][CH:22]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[CH:14]=3)[N:19]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 44218882HCID 44218882, compound

Product 1

HCID 57860960HCID 57860960, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-Benzoyl-3-[2-((R)-indan-1-ylamino)-quinolin-6-yl]-thiourea (1.5 g, 3.4 mmol) was suspended in 50 mL methanol. 4.1 mL 1N sodium hydroxide solution was added and the reaction mixture was refluxed for 2 h. The reaction mixture was diluted with 80 mL water and extracted with dichloromethane (2×100 mL). The organic phases were pooled, dried with sodium sulfate and evaporated. The residue was recrystallized from dichloromethane and diethylether. The title compound (660 mg, 58%) was obtained as an off-white solid; MS: m/e=335.3 (M+H+).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. extractionextracted with dichloromethane (2×100 mL)
  3. dry with materialdried with sodium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from dichloromethane and diethylether

Sources & evidence

ORD record
ord-27ec90231a7c454c9f15ea0d421a3a5f
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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