Hydrochloric Acid → HCID 86585204, compound

HRID 1940100Notes

Reaction equation

HRID 1940100 reaction equation
[CH3:1][O:2]C1C=CC(CCN)=CC=1.CN([C:15]1[CH:20]=CC=CN=1)C.[CH3:21][O:22][C:23]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:24]=1[C:25](Cl)=[O:26].Cl.[N:34]1C=CC=CC=1>>[CH3:1][O:2][C:30]1[C:29]([Cl:32])=[CH:28][C:24]([C:25]([NH2:34])=[O:26])=[C:23]([O:22][CH3:21])[C:31]=1[CH2:15][CH3:20]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 4657O-MethyltyramineHCID 218852-DimethylaminopyridineHCID 123841765-Chloro-2-methoxybenzoyl chloride

Product 1

HCID 86585204HCID 86585204, compound

Procedure

1.51 g (10.0 mmol) of 4-methoxy-β-phenylethylamine are dissolved in 40 ml of pyridine, a spatula-tip of dimethylaminopyridine is added and a solution of 2.15 g (10.5 mmol) of 2-methoxy-5-chlorobenzoyl chloride is added. The reaction mixture is poured onto cold dilute hydrochloric acid and the product which has precipitated is filtered off with suction and dried. 4-Methoxy-β-ethyl-(2-methoxy-5-chlorobenzamide) is obtained as colorless crystals of melting point 83°-84° C. The benzamide thus obtained is introduced into cold chlorosulfonic acid. When the reaction is complete, the reaction mixture is poured onto ice and the precipitate is filtered off with suction (melting point of the sulfonic acid chloride: 140°-141° C.) and dissolved in acetone. Excess, concentrated, aqueous ammonia is added to this solution and, when the exothermic reaction has subsided, the mixture is concentrated to one third of the original volume. 2-Methoxy-5-chloro-N-[5-(1-sulfonylamino-2-methoxyphenyl)-ethyl]-benzamide is obtained as colorless crystals of melting point 220°-222° C.

Workup

  1. customthe product which has precipitated
  2. filtrationis filtered off with suction
  3. customdried

Sources & evidence

ORD record
ord-64c506cee1464da29dd0e9c07b054c28
Source dataset
uspto-grants-1997_12
Patent number
US05698596

Reaction notes

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