Tetrahydrofuran → HCID 13335597, compound

HRID 2164610Notes

Reaction equation

HRID 2164610 reaction equation
Cl[C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[O:3]1.O1CCCC1.[NH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1.C(N(CC)CC)C>O.CN(C)C=O>[OH:3][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:23]1[CH2:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([S:32]([NH2:35])(=[O:33])=[O:34])=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 35605513-chloro-3-phenyl-1-(3H)-isobenzofuranone

Product 1

HCID 13335597HCID 13335597, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

12.35 parts of 3-chloro-3-phenyl-1-(3H)-isobenzofuranone in solution in 40 parts of anhydrous tetrahydrofuran are added, while stirring, over a period of approximately 15 minutes, to a solution of 10 parts of para-(β-aminoethyl)benzenesulphonamide and 5.06 parts of triethylamine in 80 parts of anhydrous dimethylformamide. The temperature rises from 25° to 50° C. and after being stirred for 2 hours the reaction mixture is diluted in 400 parts of water. The precipitate formed is suction-filtered and dried in air and then recrystallized in 360 parts of isopropanol. 12 parts of para-[β-(2,3-dihydro-3-hydroxy-3-phenyl-(1H)-isoindol-1-on-2-yl)ethyl]benzenesulphonamide are obtained melting at 225° C.

Workup

  1. customrises from 25° to 50° C.
  2. customThe precipitate formed
  3. filtrationis suction-filtered
  4. customdried in air
  5. customrecrystallized in 360 parts of isopropanol

Sources & evidence

ORD record
ord-fc452533e5a14bc491e214bf43f549e6
Source dataset
uspto-grants-1985_03
Patent number
US04505921

Reaction notes

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