Cyclopropanecarbonyl chloride → HCID 23341635, compound

HRID 1448706Notes

Reaction equation

HRID 1448706 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[NH2:7][C:8]1[S:9][C:10]([CH3:17])=[CH:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14]>N1C=CC=CC=1>[C:13]([C:12]1[CH:11]=[C:10]([CH3:17])[S:9][C:8]=1[NH:7][C:4]([CH:1]1[CH2:3][CH2:2]1)=[O:5])([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 675878Methyl-2-amino-5-methyl-3-thiophenecarboxylate

Product 1

HCID 23341635HCID 23341635, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cyclopropanecarboxylic acid chloride (10.9 g, 0.105 mol) was added dropwise during 40 min. to a stirred solution of methyl 2-amino-5-methyl-3-thiophene-carboxylate (prepared by the method of Gewald, Chemische Berichte, 99, 94, (1966)), (17.1 g, 0.1 mol) in anhydrous pyridine (100 ml) kept at 0° C. The reaction mixture was stirred below 10° C. for the next 4 hours, at room temperature overnight, and finally under reflux for 1.5 hours. The excess of pyridine was evaporated under reduced pressure and the residue was dissolved in CHCl3 (200 ml) and extracted in turn with 2N--HCl, H2O, 2N--NaOH and H2O. The dried (Na2SO4) organic solution was evaporated and the residue was recrystallised from EtOH to yield the amide as yellow crystals (11.1 g, 46%), m.p. 121°-123° C.

Workup

  1. customkept at 0° C
  2. temperaturefinally under reflux for 1.5 hours
  3. customThe excess of pyridine was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in CHCl3 (200 ml)
  5. extractionextracted in turn with 2N
  6. dry with materialThe dried (Na2SO4) organic solution
  7. customwas evaporated
  8. customthe residue was recrystallised from EtOH

Sources & evidence

ORD record
ord-e7320681215843ae9647dbf5c81cd26b
Source dataset
uspto-grants-1980_02
Patent number
US04187232

Reaction notes

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