Triethylamine → HCID 22571140, compound

HRID 905725Notes

Reaction equation

HRID 905725 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[O:11]=[C:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][S:20]([CH3:19])(=[O:22])=[O:21])[CH:3]=2)[NH:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27732135-Amino-2-oxindole

Product 1

HCID 22571140HCID 22571140, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

A stirred solution of 5-amino-1,3-dihydro-indol-2-one (2 g, 13.5 mmol, prepared according to U.S. Pat. No. 6,114,371) in 30 ml of dichloromethane was added with triethylamine (1.9 ml). The solution was cooled down to −30° C. in an acetone-dry ice bath and added with methanesulfonyl chloride (1 ml, 13.5 mmol) dropwise. Upon the completion of the addition, the resulting mixture was heated at 45° C. for 1 hour until precipitate was formed. The solid was filtered, washed with water (50 ml×3) and dried in vacuo to give N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-methanesulfonamide (2.7 g, 90%) as a white solid.

Workup

  1. additionUpon the completion of the addition
  2. temperaturethe resulting mixture was heated at 45° C. for 1 hour until precipitate
  3. customwas formed
  4. filtrationThe solid was filtered
  5. washwashed with water (50 ml×3)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-856fd50876624708a7c1c317437b768c
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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