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

HRID 1835541Notes

Reaction equation

HRID 1835541 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-9fed7b20efeb4fd680db9adc437dc8c1
Source dataset
uspto-grants-2004_08
Patent number
US06770648B2

Reaction notes

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