Water → Methyl 3-(2-cyanopyrrol-1-yl)benzoate

HRID 399863Notes

Reaction equation

HRID 399863 reaction equation
ClS([N:5]=[C:6]=O)(=O)=O.[N:8]1([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9]1.CN(C)C=O.O>ClCCl>[C:6]([C:12]1[N:8]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])[CH:9]=[CH:10][CH:11]=1)#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 3322314Methyl 3-(1H-pyrrol-1-yl)benzoate

Product 1

HCID 18945318Methyl 3-(2-cyanopyrrol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chlorosulfonyl isocyanate (18.2 ml) was dropwise added to a solution of methyl 3-(pyrrol-1-yl)benzoate (35.0 g) in dichloromethane (350 ml) at -10°~20° C. and the mixture was stirred for 1 hour at the same temperature. To the mixture was dropwise added N,N-dimethylformamide (105 ml) at the same temperature and the mixture was stirred for 1 hour at 0°-5° C. The reaction mixture was poured into water. The separated organic layer was washed with saturated aqueous sodium bicarbonate solution and water. The organic solution was dried over magnesium sulfate and evaporated in vacuo to give methyl 3-(2-cyanopyrrol-1-yl)benzoate (30.67 g).

Workup

  1. stirringthe mixture was stirred for 1 hour at 0°-5° C
  2. washThe separated organic layer was washed with saturated aqueous sodium bicarbonate solution and water
  3. dry with materialThe organic solution was dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-9a1d0727ce7e4f48b6f76e523f48377d
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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