Methylamine → (1-Amino-1H-pyrrol-2-yl)-2-thienylmethanone

HRID 1080464Notes

Reaction equation

HRID 1080464 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[N:9]([N:13]2C(=O)C3C(=CC=CC=3)C2=O)[CH:10]=[CH:11][CH:12]=1)=[O:7].CN>CN(C)C=O.O>[NH2:13][N:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:7]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 199731582-[2-(2-thienylcarbonyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

Product 1

HCID 19973146(1-Amino-1H-pyrrol-2-yl)-2-thienylmethanoneYield 64.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[2-(2-thienylcarbonyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione (15.43 g) in 50 ml of dimethylformamide was added 50 ml of 40% methylamine. The reaction mixture was stirred for 1.5 hours at room temperature, diluted with water and extracted with DCM. The combined organic layers were washed with water, dried over magnesium sulfate and evaporated in vacuo. The residual oil was recrystallized from ethyl ether/hexane to afford the product (5.96 g), m.p. 81°-82° C.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residual oil was recrystallized from ethyl ether/hexane

Sources & evidence

ORD record
ord-f39d3042308f4be5ac038f53d12ccbe7
Source dataset
uspto-grants-1996_12
Patent number
US05580987

Reaction notes

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