Sodium Hydroxide → Phenoxathiin

HRID 372488

Reaction equation

HRID 372488 reaction equation
C([C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=1)#N.[N-]=[N+]=[N-].[Na+].[OH-].[Na+]>CN(C)C=O>[CH:8]1[C:7]2[S:6][C:5]3[C:14](=[CH:15][CH:16]=[CH:3][CH:4]=3)[O:13][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 203841882-Cyanophenoxathiin

Product 1

HCID 9217Phenoxathiin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-cyanophenoxathiin (2.25g), sodium azide (0.68g) ammonium chloride (0.59g) and dimethylformamide (30 ml.) were heated for 9 hours at 130° C. The solution was poured onto ice and 2 Normal sodium hydroxide solution, and extracted with chloroform. The aqueous phase was acidified with concentrated hydrochloric acid. The solid was filtered, washed and dried to give 2-5-tetrazolyl)phenoxathiin m.p. 210°-2° C. Recrystallisation from glacial acetic acid raised the melting point to 220°-1° C.

Workup

  1. extractionextracted with chloroform
  2. filtrationThe solid was filtered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-e1744285232049b1864671742705fa89
Source dataset
uspto-grants-1978_05
Patent number
US04091108

Linked notes

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