Triethylamine → HCID 54376218, compound

HRID 1703500Notes

Reaction equation

HRID 1703500 reaction equation
[N+:1]([C:4]1[O:5][C:6]2[C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:7]=2[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O-:3])=[O:2].Cl.[CH2:23]([N:25]([CH2:28][CH2:29]Cl)[CH2:26][CH3:27])[CH3:24].C(N(CC)CC)C>CN(C)C=O>[N+:1]([C:4]1[O:5][C:6]2[C:18]([C:19]([O:21][CH2:24][CH2:23][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:20])=[CH:17][CH:16]=[CH:15][C:7]=2[C:8]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 20330199HCID 20330199, compound

Product 1

HCID 54376218HCID 54376218, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 14.2 g (0.05 mole) of 2-nitro-3-phenyl-7-benzofurancarboxylic acid, 8.6 g (0.05 mole) of N,N-diethylamino-2-chloroethane hydrochloride, 10.1 g (0.1 mole) of triethylamine and 75 ml of N,N-dimethylformamide is heated at 90° to 100° C. for 16 hours, then left standing at 23° C. for 2 days. The mixture is cooled with an ice bath, then filtered to remove the white solid by-product. The filtrate is dissolved in diethyl ether, washed thrice with water and twice with saturated sodium chloride solution and dried. The solution is evaporated to provide an oil, N,N-diethylaminoethyl 2-nitro-3-phenyl-7-benzofurancarboxylate. This oil is dissolved in diethyl ether and treated with 25 ml of 4N-hydrochloric acid in isopropanol to provide a product which gradually solidifies. The product is recrystallized twice from ethanol to provide, N,N-diethylaminoethyl 2-nitro-3-phenyl-7-benzofurancarboxylate hydrochloride, m.p. 194.5°-195° C., as a light yellow solid.

Workup

  1. temperatureis heated at 90° to 100° C. for 16 hours
  2. waitleft
  3. temperatureThe mixture is cooled with an ice bath
  4. filtrationfiltered
  5. customto remove the white solid by-product
  6. dissolutionThe filtrate is dissolved in diethyl ether
  7. washwashed thrice with water
  8. dry with materialtwice with saturated sodium chloride solution and dried
  9. customThe solution is evaporated

Sources & evidence

ORD record
ord-e56d52c4042941b9a4052940a3e84a1a
Source dataset
uspto-grants-1978_11
Patent number
US04124603

Reaction notes

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