Triethylamine → HCID 22117837, compound

HRID 1740430Notes

Reaction equation

HRID 1740430 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:36][NH:37][O:38][CH3:39]>ClCCl>[CH3:39][O:38][N:37]([CH3:36])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)[CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 9570674-chloro-3-(1H-pyrrol-1-yl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22117837HCID 22117837, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g of 4-chloro-3-(1H-pyrrol-1-yl)benzoic acid in 200 ml of dichloromethane were treated in succession with 3.13 ml of triethylamine and 4.33 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDAC.HCl). The mixture was stirred at room temperature until it became clear and was then cooled to 0° C. and 2.21 g of N,O-dimethylhydroxylamine hydrochloride were added. The mixture was then left to come to room temperature and was stirred for a further 18 hours, washed with 1M aqueous hydrochloric acid and with brine and then dried over anhydrous magnesium sulphate. Evaporation under reduced pressure gave 5.73 g of N-methoxy-N-methyl-4-chloro-3-(1H-pyrrol-1-yl)benzamide as a viscous oil.

Workup

  1. temperaturewas then cooled to 0° C.
  2. waitThe mixture was then left
  3. customto come to room temperature
  4. stirringwas stirred for a further 18 hours
  5. washwashed with 1M aqueous hydrochloric acid and with brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-d075852f4ea04a73aa9fd5a143a56dd0
Source dataset
uspto-grants-1999_10
Patent number
US05969139

Reaction notes

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