Bromine → Methyl 2-amino-4-methylbenzo[d]thiazole-5-carboxylate

HRID 1263407Notes

Reaction equation

HRID 1263407 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:12][C:13]([NH2:15])=[S:14].BrBr>ClC1C=CC=CC=1>[NH2:15][C:13]1[S:14][C:4]2[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:2]([CH3:1])[C:3]=2[N:12]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 18616039N-(2-Methyl-3-methoxycarbonylphenyl)thiourea

Product 1

HCID 22390084Methyl 2-amino-4-methylbenzo[d]thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
0 °C

Procedure

56 g of N-(2-methyl-3-methoxycarbonylphenyl)thiourea (0.25 mol) were dissolved in 2 l of chlorobenzene, and the mixture was cooled to 0° C. 40 g of bromine (0.25 mol) in 100 ml of chlorobenzene were then added dropwise. The reaction mixture was heated at 90° C. for 3 h, and the precipitate was filtered off with suction and washed with methylene chloride. The precipitate was then dissolved in ethyl acetate and extracted with sodium bicarbonate solution. After washing and drying, the product was obtained by stripping off the solvent. Yield: 43 g (80%).

Workup

  1. temperatureThe reaction mixture was heated at 90° C. for 3 h
  2. filtrationthe precipitate was filtered off with suction
  3. washwashed with methylene chloride
  4. dissolutionThe precipitate was then dissolved in ethyl acetate
  5. extractionextracted with sodium bicarbonate solution
  6. washAfter washing
  7. customdrying
  8. customthe product was obtained

Sources & evidence

ORD record
ord-1457830cd9ea443bbca17272e72d3e21
Source dataset
uspto-grants-2003_04
Patent number
US06541423B1

Reaction notes

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