2-Bromo-5-nitrothiazole → HCID 20333091, compound

HRID 1706905Notes

Reaction equation

HRID 1706905 reaction equation
[Na][S:2][C:3]1[C:7]([C:8]#[N:9])=[C:6]([S:10][Na])[S:5][N:4]=1.Br[C:13]1[S:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][N:17]=1>CO>[N+:18]([C:15]1[S:14][C:13]([S:2][C:3]2[C:7]([C:8]#[N:9])=[C:6]([S:10][C:13]3[S:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][N:17]=3)[S:5][N:4]=2)=[N:17][CH:16]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 182112-Bromo-5-nitrothiazoleHCID 178510538HCID 178510538, compound

Product 1

HCID 20333091HCID 20333091, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4.36 (0.02 mol.) of 3,5-di(sodiomercapto)-4-isothiazole carbonitrile in methanol was added 8.4 g (0.04 mol.) of 2-bromo-5-nitrothiazole. A yellow-brown solid begins to precipitate almost immediately. The reaction mixture is stirred for an additional 2 hours at room temperature (~22° C.). The precipitate is collected by suction filtration, washed with water and methanol and dried in vacuo to yield 6.77 g (79% yield from the isothiazole) of a tan solid, m.p. 197°-199.5° C.

Workup

  1. customto precipitate almost immediately
  2. filtrationThe precipitate is collected by suction filtration
  3. washwashed with water and methanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-81ee75c9b6064dae8e2192c767d5ce96
Source dataset
uspto-grants-1980_06
Patent number
US04209522

Reaction notes

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