Triethylamine → 1-Methanesulfonyl-6-nitroindoline

HRID 2264317Notes

Reaction equation

HRID 2264317 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:20][S:21]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH2:8][CH2:9]1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 297576-NitroindolineHCID 31297Methanesulfonyl chloride

Product 1

HCID 231122131-Methanesulfonyl-6-nitroindolineYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 ml of methylene chloride was dissolved 2.5 g of 6-nitroindoline, and then 6.37 ml of triethylamine was added thereto. Under ice cooling, 3.51 g of methanesulfonyl chloride was added dropwise, the reaction solution was stirred at room temperature for 3 hours, and then ice-water was added thereto, followed by 1 hour of stirring. The reaction solvent was removed by evaporation under reduced pressure, a 1M aqueous hydrochloric acid solution was added to the residue, and precipitated was filtrated off, whereby 3.52 g of 1-methylsulfonyl-6-nitroindoline was obtained as a brown solid.

Workup

  1. waitfollowed by 1 hour
  2. stirringof stirring
  3. customThe reaction solvent was removed by evaporation under reduced pressure
  4. additiona 1M aqueous hydrochloric acid solution was added to the residue
  5. customprecipitated
  6. filtrationwas filtrated off

Sources & evidence

ORD record
ord-99802f44378e46db9651870d6adcf145
Source dataset
uspto-grants-2010_12
Patent number
US07855198B2

Reaction notes

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