Hydrochloric Acid → Benzamide, 5-chloro-2-methoxy-N-[2-(4-nitrophenyl)ethyl]-

HRID 2187669Notes

Reaction equation

HRID 2187669 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(C1NC=CN=1)(C1NC=CN=1)=O.Cl.[N+:26]([C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][NH2:37])=[CH:31][CH:30]=1)([O-:28])=[O:27].Cl>C1COCC1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([NH:37][CH2:36][CH2:35][C:32]1[CH:31]=[CH:30][C:29]([N+:26]([O-:28])=[O:27])=[CH:34][CH:33]=1)=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 769705-Chloro-o-anisic acidHCID 458983Benzeneethanamine, 4-nitro-, hydrochloride (1:1)HCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 10782977Benzamide, 5-chloro-2-methoxy-N-[2-(4-nitrophenyl)ethyl]-Yield 87.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 8.8 g (47.2 mmol) of 5-chloro-2-methoxybenzoic acid and 8.5 g (51.9 mmol) of carbonylbisimidazole in 180 ml of absolute THF was stirred at room temperature for 2 h. 10 g (49.7 mmol) of 2-(4-nitrophenyl)ethylamine hydrochloride and 9.4 ml of triethylamine were added and the resulting solution was then stirred overnight at room temperature. The reaction solution was then slowly poured onto 1.2 l of 1N hydrochloric acid, and the deposited precipitate was filtered off and washed with water. Drying of the precipitate in a high vacuum yielded 13.8 g of the title compound as a white solid. M.p.: 159-160° C. Rf (silica gel, EA/heptane 4:1)=0.46. MS (ESI): m/z=334 (M+H)+.

Workup

  1. filtrationthe deposited precipitate was filtered off
  2. washwashed with water
  3. customDrying of the precipitate in a high vacuum

Sources & evidence

ORD record
ord-46087fc6dc3d4ffbb795a43b8bb2bf27
Source dataset
uspto-grants-2002_06
Patent number
US06410573B1

Reaction notes

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