Bromine → HCID 12790770, compound

HRID 1660150Notes

Reaction equation

HRID 1660150 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[N:5]=[C:6]([CH3:9])[S:7][CH:8]=1.C([O-])(=O)C.[Na+].[Br:15]Br>C(O)(=O)C>[Br:15][C:8]1[S:7][C:6]([CH3:9])=[N:5][C:4]=1[CH2:3][Cl:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)

Product 1

HCID 12790770HCID 12790770, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To 11 g of 4-chloromethyl-2-methylthiazole, hydrochloride (0.06 mol), dissolved in 150 ml of glacial acetic acid are added while stirring, 11.5 g of anhydrous sodium acetate (0.14 mol) and at 45°-50°, 9.6 g of bromine (0.12 mol) in 50 ml of glacial acetic acid. Stirring is continued for an additional 2.5 hours at 60°-80° C. Then the solution is evaporated in vacuo to dryness and the residual product is extracted with ether. Evaporation of the solvent gives 8.3 g oil which is then dissolved in hexane. Charcoal treatment, evaporation of the solvent, dissolving of the oil again in 100 ml of ether and addition of ethereal hydrochloric acid, yield the hydrochloride. Yield: 6.5 g (41%), m.p. 154°-156° C.

Workup

  1. additionare added
  2. customat 45°-50°
  3. stirringStirring
  4. customThen the solution is evaporated in vacuo to dryness
  5. extractionthe residual product is extracted with ether
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d60b272ffb104e7ba15bdf2c7cf0440e
Source dataset
uspto-grants-1981_12
Patent number
US04307105

Reaction notes

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