HCID 58496338, compound → HCID 58496340, compound

HRID 330808Notes

Reaction equation

HRID 330808 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=3)[C:6]=2[CH:21]=1>C1COCC1.[Pd]>[NH2:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][N:7]1[C:6]2[CH:21]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[S:9][C:8]1=[O:10]

Participants

4

Reactant 1

HCID 58496338HCID 58496338, compound

Product 1

HCID 58496340HCID 58496340, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4.5 g (12.8 mol) of 5-chloro-3-(3-nitrobenzyl)-3H-benzothiazol-2-one [“A13a”; prepared analogously to “A12”; ESI: 321 (M+H); Rt.=3.20 min (method A)] are dissolved in 100 ml of THF and hydrogenated under a hydrogen atmosphere at room temperature using 2 g of palladium on active carbon (water-moist, 5% of Pd). After 24 h, the catalyst is filtered off with suction, rinsed with THF and evaporated, giving 3-(3-aminobenzyl)-5-chloro-3H-benzothiazol-2-one, ESI: 291 (M+H); HPLC: Rt.=2.28 min (method A).

Workup

  1. customprepared analogously to “A12”
  2. customhydrogenated under a hydrogen atmosphere at room temperature
  3. filtrationthe catalyst is filtered off with suction
  4. washrinsed with THF
  5. customevaporated

Sources & evidence

ORD record
ord-8a967c90e05a42a78c86e07e134d2722
Source dataset
uspto-grants-2014_11
Patent number
US08877751B2

Reaction notes

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