2-Amino-6-nitrobenzothiazole → 2,6-Benzothiazolediamine

HRID 723943Notes

Reaction equation

HRID 723943 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=1)([O-])=O.Cl[Sn]Cl>C(O)C>[S:10]1[C:6]2[CH:5]=[C:4]([NH2:1])[CH:13]=[CH:12][C:7]=2[N:8]=[C:9]1[NH2:11]

Participants

4

Reactant 2

HCID 227042-Amino-6-nitrobenzothiazoleHCID 24479Stannous Chloride

Product 1

HCID 215042,6-BenzothiazolediamineYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-nitro-benzothiazol-2-ylamine (1.0 g, 5.12 mmol) and SnCl2 (4.86 g, 25.6 mmol) in 15 mL ethanol (denatured) was heated at reflux for 1 hour. The mixture was concentrated and partitioned between 100 mL CH2Cl2 and 50 mL 1.0 N NaOH. The organic layer was separated and the aqueous layer was extracted with 2×100 mL of CH2Cl2. The combined organic fractions were dried over MgSO4, filtered and evaporated to give a yellow solid. This was washed with a 1:1 mixture of Et2O and hexanes. Yield: 50%; 1H-NMR (acetone-d6): δ 7.14 (d, 1H, J=8.8 Hz); 6.92 (d, 1H, J=1.9 Hz); 6.62 (dd, 1H, J=1.9, 8.5 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe mixture was concentrated
  4. custompartitioned between 100 mL CH2Cl2 and 50 mL 1.0 N NaOH
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with 2×100 mL of CH2Cl2
  7. dry with materialThe combined organic fractions were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give a yellow solid
  11. washThis was washed with a 1:1 mixture of Et2O and hexanes

Sources & evidence

ORD record
ord-a4a1403136644289ad54f879c3869256
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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