Cysteamine Hydrochloride → HCID 21472114, compound

HRID 2294783Notes

Reaction equation

HRID 2294783 reaction equation
Cl.N[CH2:3][CH2:4][SH:5].[NH2:6][C:7]1[N:11]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=2[Cl:23])[N:10]=[C:9]([C:24]#[N:25])[C:8]=1[S:26]([CH3:28])=[O:27]>CO>[NH2:6][C:7]1[N:11]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:20])([F:21])[F:22])=[CH:14][C:13]=2[Cl:23])[N:10]=[C:9]([CH:24]2[NH:25][CH:3]=[CH:4][S:5]2)[C:8]=1[S:26]([CH3:28])=[O:27]

Participants

4

Reactant 2

HCID 9082Cysteamine HydrochlorideHCID 10861895HCID 10861895, compound

Product 1

HCID 21472114HCID 21472114, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.297 gram (0.00261 mole) of 2-aminoethanethiol hydrochloride in 2.5 milliliters of methanol was added to 1.0 gram (0.00261 mole) of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carbonitrile, and the mixture was stirred at room temperature for an approximately 17-hour period. The mixture was partitioned between water and dichloromethane and the organic layer was separated, dried over Na2SO4 and filtered. Solvent was evaporated leaving a residue which was purified by preparative thin-layer chromatography to give 0.186 gram (0.00042 mole) of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(dihydro-2-thiazolyl)-4-methylsulfinyl-1H-pyrazole having a melting point of 189.5° C. (with decomposition). This compound is referred to hereinafter as Compound 1.

Workup

  1. customThe mixture was partitioned between water and dichloromethane
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customSolvent was evaporated
  6. customleaving a residue which
  7. customwas purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-0f061778d7c441d3bf677d00c8726f5c
Source dataset
uspto-grants-1997_11
Patent number
US05691333

Reaction notes

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