Ammonium Chloride → HCID 178419941, compound

HRID 2355136Notes

Reaction equation

HRID 2355136 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[O:13][C:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([O:27][CH2:28][C:29]#[N:30])[CH:21]=[CH:20]3)=[CH:15][N:16]=1.[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[O:13][C:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([O:27][CH2:28][C:29]2[NH:33][N:32]=[N:31][N:30]=2)[CH:21]=[CH:20]3)=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 68451168HCID 68451168, compound

Product 1

HCID 178419941HCID 178419941, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ({6-[2-(2-naphthylmethyl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetonitrile (99 mg, 0.252 mmol), prepared in the previous step, sodium azide (50.2 mg, 0.772 mmol) and ammonium chloride (40.7 mg, 0.761 mmol) in 10 mL of DMF was stirred under nitrogen at 100° C. for three hours. Following the reaction by MS, starting material remained. Additional sodium azide (51.1 mg, 0.75 mmol) and of ammonium chloride (45.7 mg, 0.85 mmol) were added and the reaction stirred at 100° C. for two more hours. This procedure was repeated two additional times until the MS showed that the reaction went to completion. The reaction was filtered, acidified with 5 mL of 1N HC1 and then diluted with 10 mL of H2O. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (75.4 mg, 69%) as a tan solid, mp 179-182° C. Elemental Analysis for C26H19N5O2+0.31 mol H2O Calc'd: C, 71.13; H, 4.50; N, 15.95. Found: C, 70.44; H, 4.51; N, 14.98.

Workup

  1. customthe reaction by MS
  2. stirringthe reaction stirred at 100° C. for two more hours
  3. filtrationThe reaction was filtered
  4. additiondiluted with 10 mL of H2O
  5. customThe solid that formed
  6. filtrationwas collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-8b00f690790e482e83e12b2bd98e214c
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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