Sodium Chloride → 2-Chloro-6-nitrobenzothiazole

HRID 1783494Notes

Reaction equation

HRID 1783494 reaction equation
N([O-])=O.[Na+].N[C:6]1[S:7][C:8]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:9]=2[N:10]=1.[Na+].[Cl-:19]>O.OP(O)(O)=O.[O-]S([O-])(=O)=O.[Cu+2]>[Cl:19][C:6]1[S:7][C:8]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 227042-Amino-6-nitrobenzothiazoleHCID 23668193Sodium Nitrite

Product 1

HCID 754762-Chloro-6-nitrobenzothiazoleYield 95.3%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent3×HCID 1004Phosphoric AcidSolvent

Procedure

A solution of NaNO2 (3.18 g, 46.1 mmol) in water was slowly added to a solution of 2-amino-6-nitro-benzothiazole (3.00 g, 15.4 mmol) in 85% H3PO4 over a period of 30 min at 0° C. The reaction solution was stirred for 1 hour and was gradually added to a solution of CuSO4 (7.61 g, 76.8 mmol) and NaCl (13.5 g, 230 mmol) in water over a 30 min period at 0° C. The resultant suspension was allowed to warm to room temperature, stirred until gas evolution ceased, diluted with water and extracted with CH2Cl2. The extracts were combined, dried over Na2SO4 and concentrated in vacuo to provide the title compound (3.15 g, 95%), characterized by NMR and mass spectral analyses.

Workup

  1. stirringstirred until gas evolution
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d6b5b60b3cc4cb5a6a7f8bd0cf7055f
Source dataset
uspto-grants-2009_03
Patent number
US07501421B2

Reaction notes

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