P,P-Diphenylphosphinic azide → HCID 178519011, compound

HRID 1425649Notes

Reaction equation

HRID 1425649 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]([OH:22])=[N:15]1

Participants

5

Reactant 2

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

Product 1

HCID 178519011HCID 178519011, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of diphenylphosphoryl azide (6.9 ml, 32 mmol) in pyridine (50 ml) and triethylamine (4.5 ml) is added, at 0° C., 2-mercaptonicotinic acid (5 g, 32 mmol) in portions. After 30 min, the ice cooling is removed and the mixture is stirred at 25° C. for a further 16 h. The solvent is distilled off under reduced pressure and the residue, a viscous oil, is admixed with methyl tert-butyl ether. While stirring, EtOAc/H2O is added and the mixture is stirred for another 15 min. The resulting pale yellow solid is filtered off with suction and dried.

Workup

  1. customthe ice cooling is removed
  2. distillationThe solvent is distilled off under reduced pressure
  3. stirringWhile stirring
  4. additionEtOAc/H2O is added
  5. stirringthe mixture is stirred for another 15 min
  6. filtrationThe resulting pale yellow solid is filtered off with suction
  7. customdried

Sources & evidence

ORD record
ord-38af4a99d0bc4774a799647330cef376
Source dataset
uspto-grants-2015_01
Patent number
US08933024B2

Reaction notes

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