Ammonia → 2-Phenyl-benzothiazol-6-ylamine

HRID 2243077Notes

Reaction equation

HRID 2243077 reaction equation
[C:1]1([C:7]2[S:8][C:9]3[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Sn](Cl)Cl.N>Cl>[C:1]1([C:7]2[S:8][C:9]3[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24479Stannous ChlorideHCID 15126576-Nitro-2-phenylbenzothiazole

Product 1

HCID 4591172-Phenyl-benzothiazol-6-ylamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-Phenyl-6-nitrobenzothiazole (73.5 g, 0.286 mol) is added to tin dichloride (200.74 g, 0.89 mol) in 37% HCl (300 ml). The mixture is heated at 100° C. for 40 minutes. The resulting mixture is cooled and aqueous ammonia (pH=10) is added dropwise. The product is extracted with chloroform and the extracts are concentrated. The solid is recrystallized from isopropyl ether/hexane (2/1). Yield: 29.9 g (46%); Rf (9/1 chloroform/methanol): 0.68; m.p.: 199.8-201.1° C.; IR (KBr): 3450, 3305, 3190, 1619 cm−1.

Workup

  1. temperatureThe resulting mixture is cooled
  2. extractionThe product is extracted with chloroform
  3. concentrationthe extracts are concentrated
  4. customThe solid is recrystallized from isopropyl ether/hexane (2/1)

Sources & evidence

ORD record
ord-c417e7aed09446d28227beb25b199d5c
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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