1-Methylcyclopropanecarboxylic acid → HCID 45123408, compound

HRID 1446684Notes

Reaction equation

HRID 1446684 reaction equation
[CH3:1][C:2]1([C:5](O)=O)[CH2:4][CH2:3]1.[NH2:8][NH:9][C:10]([NH2:12])=[S:11].O(Cl)Cl.[P+3]>O1CCOCC1>[CH3:1][C:2]1([C:5]2[S:11][C:10]([NH2:12])=[N:9][N:8]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 813261-Methylcyclopropanecarboxylic acidHCID 2723789ThiosemicarbazideHCID 178479710HCID 178479710, compound

Product 1

HCID 45123408HCID 45123408, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Combine 1-methylcyclopropane-1-carboxylic acid (10.00 g, 99.88 mmol), and thiosemicarbazide (9.10 g, 99.88 mmol) in dioxane (110 mL). Heat the mixture to 90° C. under N2, then add phosphorus(III) oxychloride (9.14 mL, 99.88 mmol) dropwise over 25 minutes. The reaction mixture is stirred for 6 hours at 90° C., then 8 hours at room temperature. Decant onto 200 g ice and add ammonium hydroxide to make basic. Filter to remove solids; the filtrate is extracted with ethyl acetate. The organic layer is washed with water. Dry the resulting organics over magnesium sulfate, filter, and concentrate to give product (2.54 g, 16%). MS (ES), m/z 156 (M+1).

Workup

  1. custom8 hours
  2. customat room temperature
  3. customDecant onto 200 g ice
  4. additionadd ammonium hydroxide
  5. filtrationFilter
  6. customto remove solids
  7. extractionthe filtrate is extracted with ethyl acetate
  8. washThe organic layer is washed with water
  9. dry with materialDry the resulting organics over magnesium sulfate
  10. filtrationfilter
  11. concentrationconcentrate

Sources & evidence

ORD record
ord-3615bafdf9bf4fc59a7e40a3232f46dc
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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