Tetrahydrofuran → HCID 178492420, compound

HRID 1440771Notes

Reaction equation

HRID 1440771 reaction equation
[NH2:1][N:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH3:10])[NH:3]1.Cl[S:12]([N:15]=C=O)(=[O:14])=[O:13].Br.N=[C:20]1[N:24]([O:25][CH2:26][CH:27]=[CH:28][Cl:29])[CH2:23][CH2:22][S:21]1.C([N:32]([CH2:35]C)CC)C.[O:37]1CCCC1>>[Cl:29][CH:28]=[CH:27][CH2:26][O:25][N:24]1[CH2:23][CH2:22][S:21][CH:20]1[S:12]([N:15]=[N:32][C:35]([NH:1][N:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH3:10])[NH:3]1)=[O:37])(=[O:13])=[O:14]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 86749351HCID 86749351, compoundHCID 178492421HCID 178492421, compound

Product 1

HCID 178492420HCID 178492420, compound

Procedure

0.84 g (6 mmol) of 2-amino-4-methyl-6-methoxytriazine was suspended in 20 ml of dry tetrahydrofuran, and 0.85 g (6 mmol) of chlorosulfonyl isocyanate was dropwise added thereto at room temperature. A heat was generated mildly, and the reaction mixture turned to a pale yellow solution. Then, 1.64 g (6 mmol) of 2-imino-3-(3-chloroallyloxy)thiazolidine hydrobromide and 1.43 g (14 mmol) of triethylamine suspended in 15 ml of dry tetrahydrofuran were gradually added thereto, and the mixture was further stirred at room temperature for 30 minutes. The solvent was distilled off under reduced pressure, and then water was added to the obtained residue. The resulting oily substance was extracted three times with 80 ml of chloroform. The extract solution was washed once with 100 ml of water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. Obtained crystals were washed with ethyl ether and acetonitrile to obtain 1.2 g of desired 1-[3-(3-chloroallyloxy)thiazolidine-2-sulfonylimino]-3-(4-methyl-6-methoxytriazin-2-yl)urea.

Workup

  1. customat room temperature
  2. additionwere gradually added
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionwater was added to the obtained residue
  5. extractionThe resulting oily substance was extracted three times with 80 ml of chloroform
  6. washThe extract solution was washed once with 100 ml of water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off under reduced pressure
  9. customObtained crystals
  10. washwere washed with ethyl ether and acetonitrile

Sources & evidence

ORD record
ord-53184c82f31a4613b89604a7b820ae68
Source dataset
uspto-grants-1996_03
Patent number
US05500406

Reaction notes

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