Water → 2-(4-Cyanophenylamino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]thioacetamide

HRID 2089679Notes

Reaction equation

HRID 2089679 reaction equation
[C:1]([CH:3]([NH:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([O:12][CH2:13][CH2:14][OH:15])[C:5]=1[F:16])#[N:2].[NH4+]=[S:27].O>O1CCCC1.CO>[C:22]([C:21]1[CH:20]=[CH:19][C:18]([NH:17][CH:3]([C:4]2[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([O:12][CH2:13][CH2:14][OH:15])[C:5]=2[F:16])[C:1]([NH2:2])=[S:27])=[CH:25][CH:24]=1)#[N:23]

Participants

5

Reactant 2

HCID 962WaterHCID 682128854-({Cyano[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}amino)benzonitrile

Product 1

HCID 866774072-(4-Cyanophenylamino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]thioacetamideYield 61.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude product of 4-({cyano[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}amino)benzonitrile (2.77 g) obtained in Example 30 was dissolved in tetrahydrofuran (4.26 mL) and methanol (4.26 mL), and 20% aqueous ammonium sulfide solution (8.54 mL, 25 mmol) was added dropwise thereto at room temperature, and the resulting mixture was stirred at the same temperature. After completion of the reaction, water (4.26 mL) was added dropwise to the reaction mixture, and the resulting mixture was stirred at the same temperature for 0.5 hours. The precipitated solid was filtered. The filtrate obtained was sequentially washed with water and tert-butyl methyl ether, and dried to obtain the captioned compound (1.87 g) as a pale yellow solid.

Workup

  1. additionwas added dropwise to the reaction mixture
  2. stirringthe resulting mixture was stirred at the same temperature for 0.5 hours
  3. filtrationThe precipitated solid was filtered
  4. customThe filtrate obtained
  5. washwas sequentially washed with water and tert-butyl methyl ether
  6. customdried

Sources & evidence

ORD record
ord-0ea6bf27ddda4af9944ffb0c126e0f60
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

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