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Hydrochloric Acid → 5-tert-butyl-2-methoxy-N-[2-(4-methoxyphenyl)ethyl]benzamide

HRID 2227567
Notes
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Reaction equation

HRID 2227567 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][CH:4]=1.[C:12]([C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([CH:24]=1)[C:21](Cl)=[O:22])([CH3:15])([CH3:14])[CH3:13].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([CH:24]=1)[C:21]([NH:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:22])([CH3:15])([CH3:13])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4657O-Methyltyramine2×HCID 221431005-Tert-butyl-2-methoxybenzoyl chloride

Product 1

HCID 184743175-tert-butyl-2-methoxy-N-[2-(4-methoxyphenyl)ethyl]benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 1049
Pyridine
Solvent

Procedure

1.51 g (10.0 mmol) of 2-(4-methoxyphenyl)ethylamine were dissolved in 40 ml of pyridine and admixed with a spatula tip of 4-dimethylaminopyridine and then with a solution of 2.15 g (10.5 mmol) of 5-tert-butyl-2-methoxybenzoyl chloride. After the 2-(4-methoxyphenyl)ethylamine had been converted completely, the reaction mixture was poured into cold dilute hydrochloric acid, and the precipitated product was filtered off with suction and dried to give 5-tert-butyl-2-methoxy-N-[2-(4-methoxyphenyl)ethyl]benzamide as a colorless solid. The benzamide was introduced into cold chlorosulfonic acid. After the benzamide had been converted completely, the reaction mixture was poured onto ice and filtered off with suction, and the precipitate was dissolved in acetone. This solution was admixed with excess concentrated aqueous ammonia. After the exothermic reaction had subsided, the mixture was concentrated to a third of its original volume and the precipitate was filtered off with suction. The 5-[2-(5-tert-butyl-2-methoxybenzamido)ethyl]-2-methoxybenzenesulfonamide was obtained in the form of colorless crystals of melting point 165-168° C.

Workup

  1. filtrationthe precipitated product was filtered off with suction
  2. customdried

Sources & evidence

ORD record
ord-88fe54cdfec5442eadca15b57e02238c
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06414030B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes