Isoamyl Nitrite → Benzothiazolone

HRID 2291582Notes

Reaction equation

HRID 2291582 reaction equation
N1(C(C[N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:11]2=[O:19])=O)CCNCC1.N(OCCC(C)C)=O>C(Cl)(Cl)Cl>[S:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:10][C:11]1=[O:19]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 21278869HCID 21278869, compound

Product 1

HCID 13625BenzothiazoloneYield 155.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-[(1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (3.0 g) in chloroform (50 ml) was added dropwise isoamyl nitrite (7.3 ml), for a period of 10 minutes below 20° C. The mixture was stirred for 18 hours at ambient temperature. Then, the reaction mixture was extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and evaporated to give a crystalline product, which was recrystallized from a mixture of ethyl acetate and ethanol to give 3-[4-nitroso-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (2.54 g) as needles.

Workup

  1. extractionThen, the reaction mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give a crystalline product, which
  6. customwas recrystallized from a mixture of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-f80d8b6e0dc34288bae22bdcf3a75cf6
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

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