Water → 3-Chloro-4-(2-hydroxy-1-methyl-ethylamino)-benzonitrile

HRID 1629886Notes

Reaction equation

HRID 1629886 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[NH2:11][CH:12]([CH3:15])[CH2:13][OH:14].O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:11][CH:12]([CH3:15])[CH2:13][OH:14])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 51262-AminopropanolHCID 1455253-Chloro-4-fluorobenzonitrile

Product 1

HCID 630942843-Chloro-4-(2-hydroxy-1-methyl-ethylamino)-benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.00 g (25.7 mmol) 3-chloro-4-fluoro-benzonitrile are heated to 60° C. in 20 ml DMSO with 8.00 g (106.5 mmol) 2-amino-1-propanol with stirring for 2 hours. Then the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are washed with water and sat. sodium chloride solution, dried over sodium sulphate and evaporated down i. vac.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases are washed with water and sat. sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated down i

Sources & evidence

ORD record
ord-2f72629e8eed4814b55c817ce1c426ad
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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