Hydrochloric Acid → HCID 22557326, compound

HRID 984052Notes

Reaction equation

HRID 984052 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:22]2[C:27](=[O:28])[NH:26][C:25](=[O:29])[CH:24]=[N:23]2)[CH:5]=[CH:6][C:7]=1[C:8](Cl)([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:9]1[S:10][CH:11]=[CH:12][N:13]=1.[NH4+:30].[OH-].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:22]2[C:27](=[O:28])[NH:26][C:25](=[O:29])[CH:24]=[N:23]2)[CH:5]=[CH:6][C:7]=1[C:8]([NH2:30])([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:9]1[S:10][CH:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 22557342HCID 22557342, compound

Product 1

HCID 22557326HCID 22557326, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound (36) (0.00425 mol) in THF (20 ml) was added dropwise at 5° C. to NH4OH (20 ml) and the mixture was stirred at RT for 2 hours, then poured out on ice, neutralized with HCl 6N and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3). The pure fractions were collected and the solvent was evaporated. The residue was repurified by column chromatography over Kromasil C18 (eluent: CH3OH/H2O/HOAc 70/30/1). The pure fractions were collected and the solvent was evaporated. The residue was taken up in H2O and NH4OH (pH=8) was added. The precipitate was filtered off, washed with H2O and diethyl ether, and dried, yielding 0.3 g (±)-2-[3-chloro-4-[amino-(4-chlorophenyl)-2-thiazolylmethyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (compound 35).

Workup

  1. additionpoured out on ice
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue was repurified by column chromatography over Kromasil
  11. customThe pure fractions were collected
  12. customthe solvent was evaporated
  13. additionNH4OH (pH=8) was added
  14. filtrationThe precipitate was filtered off
  15. washwashed with H2O and diethyl ether
  16. customdried

Sources & evidence

ORD record
ord-c46432591ee3410597516d0570207699
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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