Sodium Bicarbonate → N2-(1-Phenylethyl)-1,3-benzothiazole-2,7-diamine

HRID 2235492Notes

Reaction equation

HRID 2235492 reaction equation
[N+:1]([C:4]1[C:12]2[S:11][C:10]([NH:13][CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:16]1([CH:14]([NH:13][C:10]2[S:11][C:12]3[C:4]([NH2:1])=[CH:5][CH:6]=[CH:7][C:8]=3[N:9]=2)[CH3:15])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 588965417-nitro-N-(1-phenylethyl)-1,3-benzothiazol-2-amine

Product 1

HCID 58896511N2-(1-Phenylethyl)-1,3-benzothiazole-2,7-diamineYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 0.165 g (0.55 mmol) of 7-nitro-N-(1-phenylethyl)-1,3-benzothiazol-2-amine in 10 mL of DMF was added 0.62 g (2.8 mmol) of stannous chloride dihydrate. The reaction was heated to 80° C. for 48 h and neutralized with saturated sodium bicarbonate. The mixture was filtered through celite and extracted with ethyl acetate. The extracts were dried in vacuo and purified by flash chromatography eluting with a 50-75% ethyl acetate/hexanes gradient mixture to give 0.016 g (11%) of the title compound as a light yellow solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. extractionextracted with ethyl acetate
  3. customThe extracts were dried in vacuo
  4. custompurified by flash chromatography
  5. washeluting with a 50-75% ethyl acetate/hexanes gradient mixture

Sources & evidence

ORD record
ord-d81079efaad04469a23f0ff0df11231f
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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