Triethylamine → n-[3-(Dimethylamino)propyl]-1-methyl-4-nitro-1h-pyrrole-2-carboxamide

HRID 907360Notes

Reaction equation

HRID 907360 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[CH:4]=[C:3]1[C:10](Cl)=[O:11].C[CH:14]([NH:16]P(OC1C=CC(Cl)=CC=1Cl)(OC)=S)C.C[CH2:31][N:32]([CH2:35][CH3:36])[CH2:33]C>C(Cl)Cl>[CH3:31][N:32]([CH3:33])[CH2:35][CH2:36][CH2:14][NH:16][C:10]([C:3]1[N:2]([CH3:1])[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[CH:4]=1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9299ZytronHCID 110631851-Methyl-4-nitro-1H-pyrrole-2-carbonyl chloride

Product 1

HCID 15625149n-[3-(Dimethylamino)propyl]-1-methyl-4-nitro-1h-pyrrole-2-carboxamideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride (0.254 g, 1.35 mmol; see Preparation 1(ii) above) in DCM (10 mL), is added dropwise to a solution of DMPA (0.153 g, 5.05 mmol) (Aldrich), NEt3 (0.152 g, 1.5 mmol), in DCM (10 mL) over 15 min. The resulting solution was allowed to stir overnight, before quenching the reaction with a 5% NaOH solution (20 mL). The DCM fraction was then dried over MgSO4, filtered and the solvent removed under reduced pressure to yield the sub-title compound (0.254 g, 74%).

Workup

  1. custombefore quenching
  2. customthe reaction with a 5% NaOH solution (20 mL)
  3. dry with materialThe DCM fraction was then dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-2e5dd268b48c466691af1a22b839d19f
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

Loading…