4-Nitrobenzenesulfonyl chloride → HCID 14534079, compound

HRID 1904895Notes

Reaction equation

HRID 1904895 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][N:21]=[CH:20]2)([O-:16])=[O:15].C(N(CC)CC)C>C(#N)C>[N+:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11])[N:21]=[CH:20]2)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 215015-Nitroindazole

Product 1

HCID 14534079HCID 14534079, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

In 100 ml of acetonitrile were dissolved 10 g of 4-nitrophenylsulfonyl chloride and 8.8 g of 5-nitroindazole and the solution was cooled to 0° C. Then, 6.8 g of triethylamine was gradually added dropwise to the solution and the mixture was allowed to stand overnight to precipitate crystals. Then, 50 ml of water was added dropwise to the system and the crystals formed were collected by filtration, washed with water and then ethyl acetate, and dried to provide 12.1 g of the desired product having a melting point of from 196° C. to 197° C.

Workup

  1. customto precipitate crystals
  2. additionThen, 50 ml of water was added dropwise to the system
  3. customthe crystals formed
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. dry with materialethyl acetate, and dried

Sources & evidence

ORD record
ord-4e913f0c4ee64194b91981382a106456
Source dataset
uspto-grants-1989_06
Patent number
US04840887

Reaction notes

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