Phenol → HCID 54082450, compound

HRID 1440770Notes

Reaction equation

HRID 1440770 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[S:9]([N:12]=C=O)(=[O:11])=[O:10].Br.N=[C:17]1[N:21]([O:22][CH2:23][CH2:24][CH3:25])[CH2:20][CH2:19][S:18]1.[C:26](#[N:28])C.[O:29]1CCCC1>C(N(CC)CC)C>[CH2:23]([O:22][N:21]1[CH2:20][CH2:19][S:18][CH:17]1[S:9]([N:12]=[N:28][C:26](=[O:29])[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:10])=[O:11])[CH2:24][CH3:25]

Participants

7

Reactant 5

HCID 996PhenolHCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 70918Chlorosulfonyl isocyanateHCID 21475771HCID 21475771, compound

Product 1

HCID 54082450HCID 54082450, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3.76 g (40.0 mmol) of phenol was dissolved in 40 ml of dry tetrahydrofuran, and 5.66 g (40.0 mmol) of chlorosulfonyl isocyanate was dropwise added thereto at -50° C. The reaction temperature was raised to room temperature, and then the reaction mixture was cooled again to -50° C. Then, 10.6 g (44 mmol) of 2-imino-3-n-propoxythiazolidine hydrobromide suspended in 20 ml of dry acetonitrile containing 8.08 g (80 mmol) of triethylamine, was added thereto. The reaction temperature was gradually raised to room temperature, and the mixture was further stirred at the same temperature for 10 minutes. Then, the solvent was distilled off under reduced pressure, and then water was added to the obtained residue. The mixture was extracted three times with 70 ml of chloroform. The chloroform layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. To the obtained residue, ethyl ether and a small amount of acetonitrile were added for crystallization. Then, the crystals were collected by filtration to obtain 14 g of phenyl N-(3-n-propoxythiazolidine-2 -sulfonylimino)carbamate. Then, 0.72 g (2.0 mmol) of the obtained carbamate was dissolved in 30 ml of dry dioxane, and 0.23 g (1.5 mmol) of 2-amino-4,6-dimethoxytriazine was added thereto. The mixture was refluxed under heating for 4 hours. The solvent was distilled off under reduced pressure, and ethyl ether and a small amount of acetonitrile were added for crystallization. Then, the crystals were collected by filtration to obtain 0.3 g of desired 1-(3-n-propoxythiazolidine-2-sulfonylimino)-3-(4,6-dimethoxytriazin-2-yl)urea.

Workup

  1. customat -50° C
  2. temperaturethe reaction mixture was cooled again to -50° C
  3. additionwas added
  4. temperatureThe reaction temperature was gradually raised to room temperature
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. additionwater was added to the obtained residue
  7. extractionThe mixture was extracted three times with 70 ml of chloroform
  8. washThe chloroform layer was washed with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThen, the solvent was distilled off under reduced pressure
  11. additionTo the obtained residue, ethyl ether and a small amount of acetonitrile were added for crystallization
  12. filtrationThen, the crystals were collected by filtration

Sources & evidence

ORD record
ord-957140e65c4d4d2ba1f3c1db8d56bc42
Source dataset
uspto-grants-1996_03
Patent number
US05500406

Reaction notes

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