O-methyl-N,N'-diisopropylisourea → HCID 86739242, compound

HRID 1388270Notes

Reaction equation

HRID 1388270 reaction equation
[CH3:1][C:2]1([CH3:15])[C@H:4](/[CH:5]=[C:6]2/[C:7](=[O:11])[O:8][CH2:9][CH2:10]/2)[C@H:3]1[C:12]([OH:14])=[O:13].[CH:16](NC(=NC(C)C)OC)(C)C>C(OCC)(=O)C>[CH3:1][C:2]1([CH3:15])[C@H:4](/[CH:5]=[C:6]2/[C:7](=[O:11])[O:8][CH2:9][CH2:10]/2)[C@H:3]1[C:12]([O:14][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 383824O-methyl-N,N'-diisopropylisoureaHCID 70502571HCID 70502571, compound

Product 1

HCID 86739242HCID 86739242, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.2 g of (1R,trans) 2,2-dimethyl-3-[(E) (dihydro-2-oxo-3-(2H)-furanylidene)-methyl]-cyclopropane-1-carboxylic acid, 3.5 g of methyl N,N'-diisopropyl-carbamimidate and about 20 ml of ethyl acetate was refluxed for 2 hours and was cooled and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with a 6-4 cyclohexane-ethyl acetate mixture to obtain 2.5 g of methyl (1R,trans) 2,2-dimethyl-3-[(E) (dihydro-2-oxo-3-(2H)-furanylidene)-methyl]-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =+65°±2.5° (c=0.6% in ethanol).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturewas cooled
  3. customevaporated to dryness
  4. customThe residue was chromatographed over silica gel
  5. washwas eluted with a 6-4 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-9439a1126a72465e90a73ab405865c0c
Source dataset
uspto-grants-1984_02
Patent number
US04431576

Reaction notes

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