4-(4-Chlorophenoxy)aniline → HCID 68705038, compound

HRID 1972259Notes

Reaction equation

HRID 1972259 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1[C:22]([NH2:23])=[CH:21][CH:20]=[C:19]([O:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH:18]=1.C[Si]([C:36]#[N:37])(C)C>II.CO>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][C:19]2[CH:18]=[CH:17][C:22]([NH:23][CH:12]([C:11]3[CH:14]=[CH:15][CH:16]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[C:36]#[N:37])=[CH:21][CH:20]=2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 75784-(4-Chlorophenoxy)anilineHCID 743423-BenzyloxybenzaldehydeHCID 82115Trimethylsilyl cyanide

Product 1

HCID 68705038HCID 68705038, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 887MethanolSolvent

Procedure

Reference to α-amino nitrile synthesis: Synlett, 2005, 8, 1325. A methanol solution (50 mL) of 3-benzyloxybenzaldehyde (5 g, 23.6 mmol), 4-amino-4-chlorodiphenyl ether (5.7 g, 25.9 mmol), iodine (120 mg, 0.47 mmol) and trimethylsilylcyanide (3.8 mL, 28.3 mmol) is stirred at room temperature for 18 h. The precipitate that formed is collected and rinsed with ethyl acetate/hexane (1:4) to obtain ˜7 g (67%) of 2-(4-(4-chlorophenoxy)phenylamino)-2-(3-(benzyloxy)phenyl)acetonitrile as a light brown solid.

Workup

  1. customThe precipitate that formed
  2. customis collected
  3. washrinsed with ethyl acetate/hexane (1:4)

Sources & evidence

ORD record
ord-0afec78f78d74b47b54f3d56cffa7041
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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