Hydrochloric Acid → Methyl 3-(2-cyano-5-dimethylaminomethylpyrrol-1-yl)benzoate

HRID 399814Notes

Reaction equation

HRID 399814 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:6]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:8][CH:9]=1)[CH3:3].Cl.ClS([N:25]=[C:26]=O)(=O)=O.[OH-].[Na+]>ClCCl.C(OCC)(=O)C.O.CN(C)C=O>[C:26]([C:7]1[N:6]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])=[CH:9][CH:8]=1)#[N:25]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70918Chlorosulfonyl isocyanateHCID 18945174Methyl 3-(2-dimethylaminomethylpyrrol-1-yl)benzoate

Product 1

HCID 18945421Methyl 3-(2-cyano-5-dimethylaminomethylpyrrol-1-yl)benzoate

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To the mixture of methyl 3-(2-dimethylaminomethyl-pyrrol-1-yl)benzoate (1.0 g) in dichloromethane (15 ml) was added 4N-hydrogen chloride in ethyl acetate solution (0.97 ml) under ice-cooling and the mixture was stirred for 5 minutes at the same temperature. To the mixture was added dropwise chlorosulfonyl isocyanate (0.4 ml) under ice-cooling and the mixture was stirred for 1 hour at the same temperature. To the mixture was added dropwise N,N-dimethylformamide (3.0 ml) under ice-cooling and the mixture was stirred for 1 hour at the same temperature. The reaction mixture was poured into a mixture of dichloromethane and water, and the separated aqueous layer was adjusted to pH 12 with 5N-sodium hydroxide solution. The aqueous layer was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give methyl 3-(2-cyano-5-dimethylaminomethylpyrrol-1-yl)benzoate (1.1 g) as an oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 1 hour at the same temperature
  4. temperaturecooling
  5. stirringthe mixture was stirred for 1 hour at the same temperature
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-56970f14cf044028a5ed8386b3a3863d
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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