Sodium Hydroxide → 2-Amino-6-methoxy-4,5,7-trimethylbenzothiazole

HRID 1463429Notes

Reaction equation

HRID 1463429 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[C:4]([CH3:11])[C:3]=1[CH3:12].[S-:13][C:14]#[N:15].[K+].BrBr.[OH-].[Na+]>C(O)(=O)C.O>[NH2:15][C:14]1[S:13][C:7]2[C:6]([CH3:8])=[C:5]([O:9][CH3:10])[C:4]([CH3:11])=[C:3]([CH3:12])[C:2]=2[N:1]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 516872Potassium thiocyanateHCID 147002344-Methoxy-2,3,5-trimethylaniline

Product 1

HCID 147002352-Amino-6-methoxy-4,5,7-trimethylbenzothiazoleYield 91.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

100 g of 1-amino-4-methoxy-2,3,5-trimethylbenzene was dissolved in 1,000 ml of acetic acid and 50 ml of water. Then 212 g of potassium thiocyanate was added to the solution at room temperature. The reaction mixture was cooled with ice and 37.5 ml of bromine was added dropwise thereto, followed by stirring for 30 minutes. The reaction mixture was neutralized with a 1N aqueous solution of sodium hydroxide. The insoluble matters thus formed were separated by filtering and washed with water. After recrystallizing from methanol/tetrahydrofuran, 123 g of the title compound was obtained.

Workup

  1. additionwas added dropwise
  2. customThe insoluble matters thus formed
  3. customwere separated
  4. filtrationby filtering
  5. washwashed with water
  6. customAfter recrystallizing from methanol/tetrahydrofuran

Sources & evidence

ORD record
ord-40766786739948c1b0d8c48a9d74ced2
Source dataset
uspto-grants-1994_04
Patent number
US05300518

Reaction notes

Loading…