Triethylamine → HCID 53858553, compound

HRID 963418Notes

Reaction equation

HRID 963418 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH:23]1([C:26](Cl)=[O:27])[CH2:25][CH2:24]1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[O:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9]([N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)[C:26]([CH:23]1[CH2:25][CH2:24]1)=[O:27])=[O:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 7928354HCID 7928354, compound

Product 1

HCID 53858553HCID 53858553, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3.19 g of furan-2-carboxylic acid (3-iodo-phenyl)-amide (Example 13bf)) are dissolved in 25 ml of methylene chloride with 2.78 ml of triethylamine and 100 mg of 4-dimethylaminopyridine. 1.60 g of cyclopropanecarbonyl chloride are added thereto and the mixture is stirred at room temperature for 5 hrs. The mixture is concentrated, poured into water and extracted three times with ethyl acetate. Chromatography on silica gel with ethyl acetate/hexane 3:7 gives 1.56 g of cyclopropanecarboxylic acid (furan-2-carbonyl)-(3-iodo-phenyl)-amide as a colourless solid. Yield: 58%. Mass spectrum: peaks inter alia at m/e: 381 (20%), 353 (28%), 313 (86%), 95 (75%), 69 (100%).

Workup

  1. concentrationThe mixture is concentrated
  2. additionpoured into water
  3. extractionextracted three times with ethyl acetate

Sources & evidence

ORD record
ord-bfded94fd95a4609862a89b01139da4c
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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