Sodium Hydroxide → 3,5-Dichloro-4-(5-trifluoromethyl-benzothiazol-2-ylsulfanyl)phenylamine

HRID 2427217Notes

Reaction equation

HRID 2427217 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Cl:11])[C:3]=1[S:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:16]=2[N:17]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>CCOC(C)=O>[Cl:11][C:4]1[CH:5]=[C:6]([NH2:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[S:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][C:16]=2[N:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 221488312-(2,6-Dichloro-4-nitro-phenylsulfanyl)-5-trifluoromethyl-benzothiazoleHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 221488813,5-Dichloro-4-(5-trifluoromethyl-benzothiazol-2-ylsulfanyl)phenylamineYield 96.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2,6-dichloro-4-nitro-phenylsulfanyl)-5-trifluoromethyl-benzothiazole (258) (840 mg, 1.98 mmol) in EtOAc (20 mL) was added tin chloride dihydrate (Aldrich, 2.15 g, 9.52 mmol) and the resulting mixture was heated to reflux for 3 hours. After cooled to room temperature, to the mixture was added excess of 4N aqueous NaOH solution and the resulting mixture was stirred for 20 minutes. The mixture was filtered through Celite pad and washed with EtOAc. The organic layer was separated, washed twice with a brine solution, dried over Na2SO4, and concentrated under vacuum to give compound 270 (755 mg, 96%) product as a pale yellow solid, which was used in the next reaction without further purification.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe mixture was filtered through Celite pad
  4. washwashed with EtOAc
  5. customThe organic layer was separated
  6. washwashed twice with a brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dd6b35d06f3e4eaa928d82d97a6c14b0
Source dataset
uspto-grants-2011_06
Patent number
US07968567B2

Reaction notes

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