Sodium Hydroxide → 4-Methoxy-1,3-benzothiazole-2,7-diamine

HRID 51867Notes

Reaction equation

HRID 51867 reaction equation
COC(=O)[NH:4][C:5]1[S:6][C:7]2[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.[OH-].[Na+]>O1CCOCC1.C(O)CO>[CH3:16][O:15][C:10]1[C:8]2[N:9]=[C:5]([NH2:4])[S:6][C:7]=2[C:13]([NH2:14])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21303404(7-Amino-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

Product 1

HCID 227369774-Methoxy-1,3-benzothiazole-2,7-diamineYield 83%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 4.28 g (16.9 mmol) (7-amino-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester in 100 ml dioxane and 50 ml ethylene glycol was added 100 ml 5 N NaOH and the mixture was heated at 100° C. for 16 h. After cooling to room temperature, the reaction mixture was concentrated in vacuo and the residue diluted with 300 ml tetrahydrofuran and stirred for 10 minutes. The mixture was filtered and the filtrate concentrated in vactio. The residue was triturated in ether to afford 2.73 g (83%) 4-methoxy-benzothiazole-2,7-diamine as a brown solid. ES-MS m/e (%): 196 (M+H+, 100). b) 4-Methoxy-N7,N7-dimethyl-benzothiazole-2,7-diamine

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionthe residue diluted with 300 ml tetrahydrofuran
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate concentrated in vactio
  6. customThe residue was triturated in ether

Sources & evidence

ORD record
ord-09326ff2c3244b29a37888684953d32d
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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