Chloride → HCID 10244234, compound

HRID 1491872Notes

Reaction equation

HRID 1491872 reaction equation
BrBr.[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C:13]#[N:14])[N:7]=1)(=O)[CH3:4].[Cl-].C(=O)(O)[O-].[Na+].[NH2:21][C:22](=[N:24][C:25]([NH2:27])=[S:26])[NH2:23]>O1CCOCC1.CO>[C:13]([CH2:12][C:8]1[N:7]=[C:6]([C:3]2[N:27]=[C:25]([N:24]=[C:22]([NH2:23])[NH2:21])[S:26][CH:4]=2)[CH:11]=[CH:10][CH:9]=1)#[N:14]

Participants

8

Reactant 5

HCID 312ChlorideHCID 24408BromineHCID 516892Sodium BicarbonateHCID 2724563AmidinothioureaHCID 10464595HCID 10464595, compound

Product 1

HCID 10244234HCID 10244234, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Bromine (0.64 ml) was added to a mixture of 2-acetyl-6-cyanomethylpyridine (2.0 g) in dioxane (30 ml) and 4N-dioxanichydrogen chloride (3.1 ml) at ambient temperature with stirring, and then the mixture was stirred for 1 hour at 50° C. To the mixture was added the sodium bicarbonate (5.2 g), methanol (30 ml) and diaminomethylenethiourea (2.2 g) at ambient temperature and the mixture was stirred for 2.5 hours at 50° C. The solvent was removed by concentration in vacuo. To the residue was added a mixture of water, tetrahydrofuran and ethyl acetate and the mixture was adjusted to pH 9.5 with potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with water to give 4-(6-cyanomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (1.5 g).

Workup

  1. stirringthe mixture was stirred for 1 hour at 50° C
  2. stirringthe mixture was stirred for 2.5 hours at 50° C
  3. customThe solvent was removed by concentration in vacuo
  4. additionTo the residue was added
  5. additiona mixture of water, tetrahydrofuran and ethyl acetate
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was triturated with water

Sources & evidence

ORD record
ord-069c31174df24bfa9ec569c8a99c4b11
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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