N,N-Dimethyl-1,3-propanediamine → Ethyl 5-(2,4-dichlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate

HRID 1729176Notes

Reaction equation

HRID 1729176 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[Cl:14][C:15]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18].CN(C)CCCN>C1(C)C(C)=CC=CC=1.O>[Cl:14][C:15]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17]([C:6]1[N:2]([CH3:1])[C:3]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:5]=1[CH3:7])=[O:18]

Participants

6

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 118467Ethyl 1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 15517716Ethyl 5-(2,4-dichlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetateYield 81.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

A solution of 50 g (0.276 mole) of ethyl 1,4-dimethyl-1H-pyrrole-2-acetate and 64 g (0.303 mole) of 2,4-dichlorobenzoyl chloride in 310 mL of xylene was heated under reflux for 4 h under argon. After cooling, a 20% solution of 3-dimethylaminopropylamine in H2O was added and stirred one hour. The organic layer was washed twice with 1N HCl, water, brine, and dried (MgSO4). Evaporation of the solvent in vacuo gave a solid which was recrystallized from methanol to give 79.39 g of product: mp 90°-92° C.; mass spectrum (Cl--CH4) m/z=354 (M+1); NMR 300 MHz (CDCl3) d 7.5 (s, 1H); 7.3 (dd, 2H); 6.0 (s, 1H); 4.2 (q, 2H); 3.9 (s, 3H); 3.65 (s, 2H); 1.6 (s, 3H); 1.25 (t, 3 H). Anal Calcd for C17H17Cl2NO3 : C, 57.64; H, 4.84; N, 3.95. Found: C, 57.52; H, 4.60; N, 3.80.

Workup

  1. temperatureunder reflux for 4 h under argon
  2. temperatureAfter cooling
  3. washThe organic layer was washed twice with 1N HCl, water, brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent in vacuo
  6. customgave a solid which
  7. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-c5d15164c8c54813b7fc42e9dd1b2057
Source dataset
uspto-grants-1994_07
Patent number
US05332736

Reaction notes

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