(5-Chloro-2-methoxyphenyl)acetonitrile → HCID 25215440, compound

HRID 1639682Notes

Reaction equation

HRID 1639682 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[Cl:14])=[N+:2]=[N-:3].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([CH2:22][C:23]#[N:24])[CH:21]=1.C[O-].[Na+]>C(O)C.C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([C:22]2[N:3]=[N:2][N:1]([C:4]3[CH:9]=[CH:8][C:7]([C:10]([F:12])([F:13])[F:11])=[CH:6][C:5]=3[Cl:14])[C:23]=2[NH2:24])[CH:21]=1

Participants

6

Reactant 3

HCID 7131175(5-Chloro-2-methoxyphenyl)acetonitrileHCID 10942334Sodium MethoxideHCID 63668480HCID 63668480, compound

Product 1

HCID 25215440HCID 25215440, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled and stirred mixture of 1-azido-2-chloro-4-trifluoromethyl-benzene (0.500 g, 1 eq) and commercial (5-chloro-2-methoxy-phenyl)-acetonitrile (0.492 g, 1.2 eq) in ethanol (4 ml) kept under nitrogen, a solution of sodium methoxide (0.183 g, 1.5 eq) in ethanol (2 ml) is added drop-wise (15 min). After the addition, the reaction mixture is allowed to reach room temperature spontaneously and stirring is then continued overnight at room temperature. The resulting reaction mixture is diluted with ethyl acetate (25 ml), washed with water (2×25 ml), dried over MgSO4 and evaporated to dryness. The yellow solid residue (0.610 g) is purified by crystallization from a mixture of dichloromethane and hexane (1:1), to afford the title compound as white solid (0.450 g, 50% yield). M.p. 152.8-153.3° C.

Workup

  1. additionAfter the addition
  2. customto reach room temperature
  3. stirringstirring
  4. customThe resulting reaction mixture
  5. washwashed with water (2×25 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe yellow solid residue (0.610 g) is purified by crystallization from a mixture of dichloromethane and hexane (1:1)

Sources & evidence

ORD record
ord-f3a67a139fcf4c4d84d6bbc3c438d8a5
Source dataset
uspto-grants-2012_02
Patent number
US08110588B2

Reaction notes

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