Hydrochloric Acid → 7-Ethyl-5-aminobenzothiazole

HRID 617273

Reaction equation

HRID 617273 reaction equation
Cl[Sn]Cl.Cl.[CH2:5]([C:7]1[C:15]2[S:14][CH:13]=[N:12][C:11]=2[CH:10]=[C:9]([N+:16]([O-])=O)[CH:8]=1)[CH3:6].[OH-].[Na+]>>[CH2:5]([C:7]1[C:15]2[S:14][CH:13]=[N:12][C:11]=2[CH:10]=[C:9]([NH2:16])[CH:8]=1)[CH3:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 227280367-Ethyl-5-nitro-1,3-benzothiazole

Product 1

HCID 227280297-Ethyl-5-aminobenzothiazoleYield 98.4%

Conditions

Temperature
25 °C

Procedure

To a solution of SnCl2 (1.5 g, 1.9 mmol) and 5.0 mL of HCl was added 7-ethyl-5-nitrobenzothiazole (0.12 g, 0.57 mmol) in a portion and resulting reaction mixture was stirred for 1 h at 25° C. The reaction mixture was basified with aqueous NaOH and extracted with EtOAc and CHCl3. Combined organic layers were dried over Na2SO4 and concentrated in vacuo, yielding an oil (0.10 g, >95%) which was identified as the desired amine (>95% pure) and subjected to a following reaction without further purification.

Workup

  1. customresulting
  2. customreaction mixture
  3. extractionextracted with EtOAc and CHCl3
  4. dry with materialCombined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-499d123d35d843c99eb7d07a04187be9
Source dataset
uspto-grants-1999_09
Patent number
US05948804

Linked notes

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