Benzenemethanamine, 3,4-dichloro- → HCID 59474755, compound

HRID 1966509Notes

Reaction equation

HRID 1966509 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]2Cl)(=[O:5])=[O:4].[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23][NH2:24]>CO>[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]2[NH:24][CH2:23][C:22]1[CH:25]=[CH:26][C:27]([Cl:28])=[C:20]([Cl:19])[CH:21]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 59474736HCID 59474736, compound

Product 1

HCID 59474755HCID 59474755, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-2-methylquinoline-8-sulfonic dimethylamide (80 mg, 0.281 mmole) and 3,4-dichlorobenzylamine (100 mg, 0.568 mmole) were stirred at 155° C. for 10 min in a microwave oven. Methanol was added and the mixture was concentrated, mixed with dichloromethane and then filtered. The residue was purified using silica gel chromatography, eluting with dichloromethane:methanol 95:5. Precipitation in ethyl acetate gave a pink solid (15 mg, 13%).

Workup

  1. concentrationthe mixture was concentrated
  2. additionmixed with dichloromethane
  3. filtrationfiltered
  4. customThe residue was purified
  5. washeluting with dichloromethane:methanol 95:5
  6. customPrecipitation in ethyl acetate

Sources & evidence

ORD record
ord-a0e3960596a34de0a31b3fece07f5b39
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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