Sodium Chloride → CID 86697018

HRID 588598Notes

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

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, iso-hexanes/ethyl acetate 4:1, then CH2Cl2/ethyl acetate 1:0 to 4:1) yielding the title compound as a solid (3.0 g).

Workup

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

Sources & evidence

ORD record: ord-b815a9652b30464fb5a2d3e5dccadb75
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227976B2

Reaction notes

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