Hydrochloric Acid → HCID 86745931, compound

HRID 487002Notes

Reaction equation

HRID 487002 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[CH:10]=[S:11]([CH3:14])([CH3:13])=[O:12])=[CH:4][CH:3]=1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[C:10](=[S:11]([CH3:13])([CH3:14])=[O:12])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 86745929HCID 86745929, compound

Product 1

HCID 86745931HCID 86745931, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 7.72 grams (0.03 mole) of N-(4-chlorophenyl)-2-(dimethyloxosulfuranylidene)acetamide, prepared in Part A of this Example, in 80 milliliters of anhydrous acetonitrile, was added 1.70 grams (0.02 mole) of ethyl chloroformate dropwise at room temperature and the resulting mixture then heated and stirred at 50° C. for an approximate 16-hour period. The hydrochloride by-product was filtered off and the filtrate vacuum evaporated to give a yellow solid. The latter was digested with cold 2N HCl to remove unreacted starting material and the undissolved solid was collected and recrystallized from methanol. Vacuum drying of the resulting solid gave 2.73 grams (0.008 mole) of ethyl 3-[(4-chlorophenyl)amino]-2-(dimethyloxosulfuranylidene)-3-oxopropanoate having a melting point of 162° C.-163° C. Elemental analysis of the product indicated the following:

Workup

  1. temperaturethe resulting mixture then heated
  2. filtrationThe hydrochloride by-product was filtered off
  3. customthe filtrate vacuum evaporated
  4. customto give a yellow solid
  5. customto remove unreacted
  6. customthe undissolved solid was collected
  7. customrecrystallized from methanol
  8. customVacuum drying of the resulting solid

Sources & evidence

ORD record
ord-f204453b3f1e4dca94ee9a2d74fb93a5
Source dataset
uspto-grants-1994_03
Patent number
US05292937

Reaction notes

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