Tetrahydrofuran → HCID 54245694, compound

HRID 1451200Notes

Reaction equation

HRID 1451200 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.Cl[S:13]([N:16]=C=O)(=[O:15])=[O:14].N=[C:20]1[N:24]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23][CH2:22][S:21]1.C([N:31]([CH2:34]C)CC)C.[O:36]1CCCC1>>[CH2:25]([N:24]1[CH2:23][CH2:22][S:21][CH:20]1[S:13]([N:16]=[N:31][C:34]([NH:1][C:2]1[N:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[N:7]=1)=[O:36])(=[O:14])=[O:15])[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 21475745HCID 21475745, compound

Product 1

HCID 54245694HCID 54245694, compound

Conditions

Temperature
0 °C

Procedure

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 40 ml of dry tetrahydrofuran, and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was dropwise added thereto at -40° C. The reaction temperature was raised to 0° C., and then the reaction mixture was cooled again to--60° C. Then, 1.90 g (12 mmol) of 2-imino-3-n-butylthiazolidine suspended in 40 ml of dry tetrahydrofuran containing 1.33 g (13 mmol) of triethylamine, was added thereto. The reaction temperature was raised to room temperature, and the mixture was further stirred at the same temperature for one hour. Then, the solvent was distilled off under reduced pressure. Then, water was added to the residue, and the mixture was extracted three times with chloroform. The chloroform layer was washed sequentially with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The obtained crystals were washed with ethyl ether to obtain 2.8 g of desired 1-(3-n-butylthiazolidine-2-sulfonylimino)-3-(4,6-dimethoxypyrimidin-2-yl)urea. Melting point: 139°-140° C.

Workup

  1. customat -40° C
  2. temperaturethe reaction mixture was cooled again to--60° C
  3. additionwas added
  4. temperatureThe reaction temperature was raised to room temperature
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. additionThen, water was added to the residue
  7. extractionthe mixture was extracted three times with chloroform
  8. washThe chloroform layer was washed sequentially with water
  9. dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate
  10. distillationThen, the solvent was distilled off under reduced pressure
  11. washThe obtained crystals were washed with ethyl ether

Sources & evidence

ORD record
ord-4e802c99a2fc4696a1e4ad85b65661b3
Source dataset
uspto-grants-1997_02
Patent number
US05604179

Reaction notes

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