p-Toluenesulfonic acid → 2-(m-Chlorophenyl)-2-morpholinoacetonitrile

HRID 1763606Notes

Reaction equation

HRID 1763606 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[C-:27]#[N:28].[K+]>C(Cl)Cl.CCCCCC>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)[C:27]#[N:28]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 69962-ChlorobenzaldehydeHCID 8083MorpholineHCID 9032Potassium Cyanide

Product 1

HCID 38104752-(m-Chlorophenyl)-2-morpholinoacetonitrile

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

As in Example 35, the following reactions are carried out. o-Chlorobenzaldehyde is reacted with p-toluenesulfonic acid, morpholine and KCN to give α-(o-chlorophenyl)-4-morpholineacetonitrile as crystals (from CH2Cl2 -hexane), m.p. 40°-42° C.

Sources & evidence

ORD record
ord-0c0d8e2031194cf8b09f01418a99ff40
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Reaction notes

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