Magnesium chloride hexahydrate → 4-Bromo-2-methylthiobenzamide

HRID 41670

Reaction equation

HRID 41670 reaction equation
[SH-:1].[Na+].O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].[Br:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([CH3:21])[CH:14]=1>CN(C)C=O>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]([NH2:18])=[S:1])=[C:15]([CH3:21])[CH:14]=1

Participants

5

Reactant 3

HCID 24644Magnesium chloride hexahydrateHCID 28015Sodium hydrosulfideHCID 1442674-Bromo-2-methylbenzonitrile

Product 1

HCID 450407164-Bromo-2-methylthiobenzamideYield 7.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry solution of sodium hydrosulphide (2.80 g, 50 mmol) and magnesium chloride hexahydrate (5.05 g, 25 mmol) in dimethylformamide (50 ml) is added 4-bromo-2-methyl benzonitrile (4.90 g, 50 mmol) in one portion and the resulting green slurry is stirred at room temp for 90 minutes. The reaction mixture is poured onto water (200 ml) and the resultant precipitate filtered and washed with water. This yellow solid is then suspended in 2N HCl (200 ml) and stirred for 1 hour, then filtered, washed with water and hexane and dried in vacuo to give 4-bromo-2-methyl-thiobenzamide (820 mg).

Workup

  1. additionThe reaction mixture is poured onto water (200 ml)
  2. filtrationthe resultant precipitate filtered
  3. washwashed with water
  4. stirringstirred for 1 hour
  5. filtrationfiltered
  6. washwashed with water and hexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-48bd0dd0b0c445288e15b03541b8230a
Source dataset
uspto-grants-2013_09
Patent number
US08530667B2

Linked notes

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