2-[(3-Nitrophenoxy)methyl]-1,3-benzothiazole → HCID 13631156, compound

HRID 1981953Notes

Reaction equation

HRID 1981953 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:13]=[C:14]([N+:18]([O-])=O)[CH:15]=[CH:16][CH:17]=1>Cl.[Fe]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[NH2:18]

Participants

4

Reactant 1

HCID 136311552-[(3-Nitrophenoxy)methyl]-1,3-benzothiazole

Product 1

HCID 13631156HCID 13631156, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of 3-[(2-benzthiazolyl)methoxy]nitrobenzene (18.6 g) in ethanolic hydrochloric acid is added powdered iron. The reaction is stirred overnight at room temperature. After neutralization with saturated aqueous sodium bicarbonate, the mixture is extracted with methylene chloride (3X). The extract is dried over magnesium sulfate and concentrated to give 15.1 g (90% yield) of product. m.p. 117°-120° C.

Workup

  1. additionis added
  2. extractionAfter neutralization with saturated aqueous sodium bicarbonate, the mixture is extracted with methylene chloride (3X)
  3. dry with materialThe extract is dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-759973ecd8d94acb8de896b3d44a3f8b
Source dataset
uspto-grants-1986_06
Patent number
US04594425

Reaction notes

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