Water → HCID 69264583, compound

HRID 888116Notes

Reaction equation

HRID 888116 reaction equation
Cl.[CH3:2][C:3]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH2:4]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].O>C(Cl)Cl>[CH3:16][S:17]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=2)[C:3]([CH3:15])([CH3:2])[CH2:4]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 69260892HCID 69260892, compound

Product 1

HCID 69264583HCID 69264583, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 3,3-dimethyl-6-nitroindoline hydrochloride (2.9 g, 12.8 mmol) in CH2Cl2 (75 mL) was added TEA (4.48 mL, 32.2 mmol) and methanesulfonyl chloride (1.1 mL, 13.5 mmol) at 0° C. The resulting mixture was stirred at RT for 4 h and water was added. Mixture was extracted with CH2Cl2, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford 1-Methanesulfonyl-3,3-dimethyl-6-nitro-2,3-dihydro-1H-indole as a yellow solid.

Workup

  1. extractionMixture was extracted with CH2Cl2
  2. dry with materialthe resulting organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-918cc7e3ba734c68a5348e9937df7eb2
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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