Ammonium Chloride → HCID 178419470, compound

HRID 1820845Notes

Reaction equation

HRID 1820845 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:23][CH2:24][C:25]#[N:26].[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:23][CH2:24][C:25]1[NH:29][N:28]=[N:27][N:26]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68982994HCID 68982994, compound

Product 1

HCID 178419470HCID 178419470, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of {[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}acetonitrile (277 mg, 0.658 mmol), prepared in the previous step, sodium azide (128 mg, 1.96 mmol) and ammonium chloride (110 mg, 2.05 mmol) in 15 mL of DMF was stirred under nitrogen at 100° C. for 4 h. The reaction was filtered and then 5 mL of 1 N HCl added to the filtrate followed by the addition of 20 mL of water. The solid present was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (276 mg, 82%) as an off-white solid, mp 227-231° C. Elemental Analysis for C21H14BrN5OS+0.48 C3H7NO+0.47H2O Calc'd: C, 53.07; H, 3.63; N, 15.11. Found: C, 53.08; H, 3.61; N, 14.91.

Workup

  1. filtrationThe reaction was filtered
  2. addition5 mL of 1 N HCl added to the filtrate
  3. additionfollowed by the addition of 20 mL of water
  4. filtrationThe solid present was collected by filtration
  5. washrinsed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4b4b0e3b361d443a85d21c1948cd7ebf
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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