Sodium Chloride → CID 86697018

HRID 1615716Notes

Reaction equation

HRID 1615716 reaction equation
[N:1]([O-])=O.[Na+].[CH]Cl.[C:7]1([C:13]2[C:17]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:16]([NH2:26])[NH:15][N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Na+].[Cl-:28]>C(Cl)Cl>[Cl:28][C:18]1[C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:1][N:26]=[C:16]2[NH:15][N:14]=[C:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:17]=12

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6432229CID 6432229HCID 23668193Sodium NitriteHCID 178509104HCID 178509104, compound

Product 1

HCID 86697018CID 86697018Yield 46.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium nitrite (2.88 g, 42 mmol) was added portionwise to cHCl (314 mL) at −15° C. and stirred for 15 min. 3-phenyl-4-(2-phenylethynyl)-1H-pyrazol-5-amine (5.4 g, 21 mmol) was added as a solid, followed by the addition of CH2Cl2 (10 mL). The reaction mixture was allowed to warm up and stirred at room temperature for 1 h. The reaction mixture was diluted with CH2Cl2 (44 mL) and NaCl (2.7 g) was added. The reaction mixture was heated to 50° C. for 1 d. The layers were separated and the organic layer was washed with water, dried (phase separator cartridge) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 4:1, then CH2Cl2/ethyl acetate 1:0 to 4:1) yielding the title compound as a solid (3.0 g).

Workup

  1. temperatureto warm up
  2. stirringstirred at room temperature for 1 h
  3. additionwas added
  4. customThe layers were separated
  5. washthe organic layer was washed with water
  6. customdried (phase separator cartridge)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 4:1

Sources & evidence

ORD record
ord-9acb7dcf64434eefa83450cdd9f0cfa5
Source dataset
uspto-grants-2014_07
Patent number
US08765762B2

Reaction notes

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