Bromoacetone → HCID 20188851, compound

HRID 1789195Notes

Reaction equation

HRID 1789195 reaction equation
O.[NH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[S:11][CH2:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1.N1[C:24]2C=CC=[CH:28][C:23]=2N=C1SCC1C(N)=NC=CC=1.BrCC(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:28][C:23]1[N:19]=[C:14]2[C:13]([CH2:12][S:11][C:3]3[NH:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[N:2]=3)=[CH:18][CH:17]=[CH:16][N:15]2[CH:24]=1

Participants

5

Reactant 3

HCID 11715BromoacetoneHCID 516892Sodium BicarbonateHCID 69793526HCID 69793526, compound

Product 1

HCID 20188851HCID 20188851, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.8 g (15 mmole) of 3-[(1H-benzimidazol-2-ylthio)methyl]-2-pyridinamine hemihydrate (see Example 1), 2.4 g (18 mmole) of bromoacetone, and 2.1 g (25 mmole) of sodium bicarbonate in 50 ml of ethanol was stirred at room temperature. After 18 hours the mixture was concentrated in vacuo to a residue that was partitioned between dilute hydrochloric acid and dichloromethane. The aqueous layer was made alkaline with potassium carbonate and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to an oil. Chromatography on basic alumina (using ethanol-toluene as eluent) yielded 1.6 g of the title compound. Structure assignment was supported by the nmr and infrared spectra.

Workup

  1. concentrationAfter 18 hours the mixture was concentrated in vacuo to a residue that
  2. customwas partitioned between dilute hydrochloric acid and dichloromethane
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-b30781462e834610ab3fc2e2c3d31c48
Source dataset
uspto-grants-1987_08
Patent number
US04687775

Reaction notes

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