Water → HCID 178522022, compound

HRID 1361013

Reaction equation

HRID 1361013 reaction equation
[C:1]1(C(N)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N-:14]=[N+:15]=[N-:16].[Na+].[Cl-].[NH4+:19].O.[CH3:21][N:22](C)[CH:23]=[O:24]>>[NH:14]1[C:5]([C:10]2[CH:9]=[C:21]([NH:22][C:23]([C:3]3[CH:2]=[CH:1][C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=3)=[O:24])[CH:3]=[CH:2][CH:1]=2)=[N:19][N:16]=[N:15]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 752441-Naphthalenecarboxamide

Product 1

HCID 178522022HCID 178522022, compoundYield 84%

Conditions

Temperature
125 °C

Procedure

The above naphthoic acid amide (10 g, 37 mmol) was dissolved in N,N-dimethylformamide (200 mL) and sodium azide (2.63 g, 40 mmol) and ammonium chloride (2.16 g, 40 mmol) were added and the mixture heated at 125° C. for 6 hours. Sodium azide (1.2 g) and ammonium chloride (0.98 g) were added and the mixture heated at 125° C. for 16 hours. After cooling, the mixture was poured into water (1.5 l) and stirred at room temperature for 30 minutes. The solid formed was filtered off, washed with water and dried in vacuo at 50° C. for 3 days affording 9.69 g (84%) of the title compound as a solid which could be further purified by treatment with ethanol at reflux temperature.

Workup

  1. temperaturethe mixture heated at 125° C. for 16 hours
  2. temperatureAfter cooling
  3. customThe solid formed
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried in vacuo at 50° C. for 3 days

Sources & evidence

ORD record
ord-ad7e8a19ac1b4ecbaef897dc545dbbd1
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Linked notes

Loading…