Sodium Chloride → CID 86717276

HRID 2205779Notes

Reaction equation

HRID 2205779 reaction equation
[N:1]([O-])=O.[Na+].[CH]Cl.[CH3:7][C:8]1[C:12]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([NH2:21])[NH:10][N:9]=1.[Na+].[Cl-:23]>C(Cl)Cl>[Cl:23][C:13]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:1][N:21]=[C:11]2[NH:10][N:9]=[C:8]([CH3:7])[C:12]=12

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6432229CID 6432229HCID 23668193Sodium NitriteHCID 178434676HCID 178434676, compound

Product 1

HCID 86717276CID 86717276Yield 45.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium nitrite (2.3 g, 33.8 mmol) was added portionwise to cHCl (33 mL) at −15° C. and stirred for 15 min. 3-methyl-4-(phenylethynyl)-1H-pyrazol-5-amine (3.3 g, 16.9 mmol) was added as a solid, followed by the addition of CH2Cl2 (5 mL). The reaction mixture was allowed to warm up and stirred at room temperature for 1 h. The reaction mixture was diluted with CH2Cl2 (28 mL) and NaCl (1.0 g) was added. The reaction mixture was heated to 50° C. for 16 h, then cooled to room temperature and partitioned between water and CH2Cl2. The organic layer was washed with water and brine, dried (phase separator cartridge) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, CH2Cl2, then CH2Cl2/ethyl acetate 9:1) yielding Compound Iu as a light yellow solid (1.9 g).

Workup

  1. temperatureto warm up
  2. stirringstirred at room temperature for 1 h
  3. additionwas added
  4. temperaturecooled to room temperature
  5. custompartitioned between water and CH2Cl2
  6. washThe organic layer was washed with water and brine
  7. customdried (phase separator cartridge)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (silica gel, CH2Cl2

Sources & evidence

ORD record
ord-6ce5abf797a7495a8e639957dba6e9d9
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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