Ammonium Chloride → HCID 178505937, compound

HRID 658409Notes

Reaction equation

HRID 658409 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:17]=[N:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].[Cl-].[NH4+].[N-:20]=[N+:21]=[N-:22].[Na+]>>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:17]=[N:16][CH:15]=[CH:14][C:11]=1[C:12]1[NH:22][N:21]=[N:20][N:13]=1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 59026796HCID 59026796, compound

Product 1

HCID 178505937HCID 178505937, compound

Conditions

Temperature
100 °C

Procedure

3-[(2-fluoro-4-iodophenyl)amino]isonicotinonitrile (100 mg, 0.29 mmol), ammonium chloride (28 mg, 0.52 mmol), and sodium azide (35 mg, 0.54 mmol) were dispended into a seal tube equipped with a stirring bar. The seal tube was degassed by vacuum and recharging with nitrogen three times before addition of anhydrous DMF (3 mL). The mixture was heated at 100° C. for three days. The mixture was diluted with saturated NaHCO3 and washed with EtOAc. The aqueous phase was acidified with concentrated HCl to pH<1, and washed with EtOAc. The aqueous layer was dried to give the desired product. LC/MS [Method B: rt: 6.008 min; m/z: 383 (M+1)].

Workup

  1. customequipped with a stirring bar
  2. customThe seal tube was degassed by vacuum
  3. additionrecharging with nitrogen three times before addition of anhydrous DMF (3 mL)
  4. additionThe mixture was diluted with saturated NaHCO3
  5. washwashed with EtOAc
  6. washwashed with EtOAc
  7. customThe aqueous layer was dried

Sources & evidence

ORD record
ord-92c4338a00114a999f7d00bdb1038c13
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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