Triethylamine → HCID 178502904, compound

HRID 2358029Notes

Reaction equation

HRID 2358029 reaction equation
Cl.[CH3:2][O:3][NH2:4].CS[C:7](=[N:11][C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[NH:8][C:9]#[N:10].C([N:21](CC)CC)C>C(O)C.O>[CH3:2][O:3][NH:4][N:8]([C:9]#[N:10])[C:7]([NH:11][C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1)=[NH:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 18770570HCID 18770570, compound

Product 1

HCID 178502904HCID 178502904, compoundYield 0.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

169.2 mg (20 mMol) O-methylhydroxylamine hydrochloride and 2.0 g (8.3 mMol) S-methyl-N-cyano-N′-(6-chloropyrid-3-yl)isothiourea are added to 50 ml ethanol and treated with 1.27 ml (9.1 mMol) triethylamine and 50.0 ml water. The reaction mixture is then stirred for ca. 18 hours at 60° C. under a protective gas (argon). At the end of the reaction the ethanol is distilled off under reduced pressure and the aqueous residue is extracted three times with chloroform. After drying the organic phase is evaporated to dryness under reduced pressure and the residue is purified by preparative HPLC. 13.5 mg (0.7%) N-methoxyamino-N′-(6-chloropyrid-3-yl)cyanoguanidine are obtained.

Workup

  1. distillationis distilled off under reduced pressure
  2. extractionthe aqueous residue is extracted three times with chloroform
  3. customAfter drying the organic phase
  4. customis evaporated to dryness under reduced pressure
  5. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-78bec9b78c7f481cb3da3131299dcf2d
Source dataset
uspto-grants-2010_07
Patent number
US07763640B2

Reaction notes

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