Water → HCID 178420093, compound

HRID 1361020Notes

Reaction equation

HRID 1361020 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[C:1]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:2]=[CH:3][C:4]([O:7][CH2:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]3[NH:25][N:24]=[N:23][N:14]=3)=[CH:11][CH:10]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 7919523HCID 7919523, compound

Product 1

HCID 178420093HCID 178420093, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

The above benzonitrile (3.00 g, 10.5 mmol) was dissolved in N,N-dimethylformamide (50 mL), and sodium azide (1.03 g, 15.8 mmol) and ammonium chloride (0.84 g, 15.8 mmol) were added and the mixture was stirred 16 hours at 125° C. The mixture was cooled to room temperature and water (50 mL) was added. The suspension was stirred overnight, filtered, washed with water and dried in vacuo at 50° C. for 3 days to give crude 3.07 g (89%) of the title compound. From the mother liquor crystals were collected and washed with water, dried by suction to give 0.18 g (5%) of the title compound as a solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringThe suspension was stirred overnight
  3. filtrationfiltered
  4. washwashed with water
  5. customdried in vacuo at 50° C. for 3 days

Sources & evidence

ORD record
ord-f7519adc4ac64dbbadd780fd56ed37b0
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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