P,P-Diphenylphosphinic azide → Isothiazolo[5,4-b]pyridin-3-ol

HRID 1775500Notes

Reaction equation

HRID 1775500 reaction equation
C1(P([N:15]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[SH:18][C:19]1[N:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22]>N1C=CC=CC=1.C(N(CC)CC)C>[S:18]1[C:19]2=[N:27][CH:26]=[CH:25][CH:24]=[C:20]2[C:21](=[O:22])[NH:15]1

Participants

5

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 178524460HCID 178524460, compound

Product 1

HCID 2727563Isothiazolo[5,4-b]pyridin-3-olYield 89%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of diphenylphosphoryl azide (39.41 g, 0.139 mol) in pyridine (160 ml) and triethylamine (19 ml) was added 2-mercaptonicotinic acid (21.57 g, 0.139 mol) portionwise at 0° C. The reaction mixture was stirred overnight at room temperature and afterwards concentrated in vacuo. Ethanol (15 ml) was added at 30° C. to the crude product. Filtration at room temperature afforded a yellow solid which was washed with ethanol (15 ml) and dried in vacuo (10 mbar). 17.04 g (89%) of the title compound were obtained as light yellow solid.

Workup

  1. concentrationafterwards concentrated in vacuo
  2. additionEthanol (15 ml) was added at 30° C. to the crude product
  3. filtrationFiltration at room temperature
  4. customafforded a yellow solid which
  5. washwas washed with ethanol (15 ml)
  6. customdried in vacuo (10 mbar)

Sources & evidence

ORD record
ord-8dbf5194d42c479389addca6a513003b
Source dataset
uspto-grants-2016_02
Patent number
US09260454B2

Reaction notes

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