Sodium hydride → 2-Benzothiazylsulfenamide

HRID 1154863Notes

Reaction equation

HRID 1154863 reaction equation
ClC1C=CC(C(F)(F)F)=CC=1[NH:12]C1C(C(F)(F)F)=CC([N+]([O-])=O)=CC=1[N+]([O-])=O.[S:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[C:30]1[S:38]Cl.[H-].[Na+]>C1COCC1.C(Cl)(Cl)(Cl)Cl>[S:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[C:30]1[S:38][NH2:12]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 113101872-Benzothiazolesulfenyl chlorideHCID 12797626Fentrifanil

Product 1

HCID 986482-Benzothiazylsulfenamide

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The sulfenylated diphenylamine was prepared from N-[2-chloro-5-(trifluoromethyl)phenyl]-2,4-dinitro-6-(trifluoromethyl)benzenamine (4.3 g, 0.010 mol) in dry THF (20 ml), 2-benzothiazolesulfenyl chloride [2.0 g, 0.010 mol, Zh. Obshch. Khim. 45, 1127 (1975)] in carbon tetrachloride (45 ml) and 50% NaH (0.53 g, 0.011 mol) as outlined in Example 1 with the following exception: the reaction mixture was stirred at 0° for 3 hours and then at room temperature for 16 hours. Purification by dry column chromatography (silica gel, hexane/ethyl acetate, 8.5/1.5) gave N-[2-chloro-5-(trifluoromethyl)-phenyl]-N-[2,4-dinitro-6-trifluoromethyl)phenyl]-2-benzothiazolesulfenamide as a red-orange glass: mp 46°-53°; NMR (CDCl3) δ 7.20-8.25 (m, 7H, Ar-H), 8.8-9.05 (AB quartet, 1.6H, Ar-H); IR(KBr) 1600, 1540, 1500, 1330, 1270, 1170, 1150, 1130 and 1070 cm-1.

Workup

  1. waitat room temperature for 16 hours
  2. customPurification
  3. dry with materialby dry column chromatography (silica gel, hexane/ethyl acetate, 8.5/1.5)

Sources & evidence

ORD record
ord-12513c75be2f45f3b158d51c17c7ef8c
Source dataset
uspto-grants-1981_11
Patent number
US04298613

Reaction notes

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