Bromine → Methyl 2-amino-6-methylbenzothiazole-4-carboxylate

HRID 1253200Notes

Reaction equation

HRID 1253200 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[S-:13][C:14]#[N:15].[K+].BrBr>C(O)(=O)C>[NH2:15][C:14]1[S:13][C:11]2[C:2](=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:1]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 1201104Methyl 2-Amino-5-methylbenzoate

Product 1

HCID 19894946Methyl 2-amino-6-methylbenzothiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

50 g (0.303 mol) of methyl 2-amino-5-methylbenzoate are dissolved in 300 ml of glacial acetic acid, and 120.6 g (1.24 mol) of potassium thiocyanate--dissolved in 200 ml of glacial acetic acid--are added. At 10° C., 17.42 ml (0.335 mol) of bromine are added dropwise, and the mixture is then stirred without cooling for 2 hours. The suspension is tipped into 3 l of ice-water, while stirring, and the precipitated product is filtered off with suction and washed with dilute sodium carbonate solution and water. The filter cake is suspended in H2O and the suspension is stirred at 100° C. overnight. After cooling, the product is filtered off with suction, washed with H2O and dried at 40° C. in vacuo.

Workup

  1. additionare added
  2. temperaturewithout cooling for 2 hours
  3. stirringwhile stirring
  4. filtrationthe precipitated product is filtered off with suction
  5. washwashed with dilute sodium carbonate solution and water
  6. stirringthe suspension is stirred at 100° C. overnight
  7. temperatureAfter cooling
  8. filtrationthe product is filtered off with suction
  9. washwashed with H2O
  10. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-8cfc8b5c4bef4a6cbff2d529ed377593
Source dataset
uspto-grants-1988_05
Patent number
US04748163

Reaction notes

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