Hydrochloric Acid → HCID 54127738, compound

HRID 963414Notes

Reaction equation

HRID 963414 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1.Cl.[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1>CN(C)C1C=CN=CC=1>[CH:16]1([C:19]([N:5]([C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([I:1])[CH:3]=2)[C:25]([CH:24]2[CH2:23][CH2:27]2)=[O:26])=[O:20])[CH2:18][CH2:17]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 122713-IodoanilineHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 54127738HCID 54127738, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

13ay) A mixture of 1.53 g of 3-iodoaniline, 2.02 g of triethylamine and 0.1 g of 4-dimethylaminopyridine in 25 ml of THF is treated dropwise with 1.83 g of cyclopropanecarbonyl chloride and subsequently held at reflux for 4 hrs. The mixture is poured into 50 ml of ice-water, made weakly acid (pH about 4) with dil. HCl and extracted three times with ethyl acetate. Chromatography on silica gel with petroleum ether/ethyl acetate 4:1 gives 1.73 g (69%) of crude cyclopropanecarboxylic acid cyclopropanecarbonyl-(3-iodo-phenyl)-amide as a colourless oil with solidifies after a few days. Yield: 69%.

Workup

  1. temperatureat reflux for 4 hrs
  2. extractionextracted three times with ethyl acetate

Sources & evidence

ORD record
ord-d8c4d56f3bee40c4bd864b3e5b6fe670
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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