Toluene → HCID 13647642, compound

HRID 1906562Notes

Reaction equation

HRID 1906562 reaction equation
[C:1]1([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.O1CCCC1.ClS([N:33]=[C:34]=[O:35])(=O)=O>O>[C:1]1([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[N:13]3[C:34]([NH2:33])=[O:35])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 70918Chlorosulfonyl isocyanateHCID 105363846-Phenyl-1,3-dihydro-indol-2-one

Product 1

HCID 13647642HCID 13647642, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To 4.5 g. (21.5 mmole) of 6-phenyl-2-oxindole in a mixture of 100 ml. of toluene and 25 ml. of tetrahydrofuran was added, with stirring, at 5° C., 2.2 ml. (25.8 mmole) of chlorosulfonyl isocyanate. Stirring was continued for 1 hour at 0°-5° C. and then 100 ml. of water was added. The solid was recovered by filtration and added to a mixture of 40 ml. of glacial acetic acid and 80 ml. of water. The resulting mixture was heated at 100° C. for 1 hour, cooled and filtered. The residue was dried to give 3.1 g. of the title compound, mp. 188°-189° C.

Workup

  1. stirringStirring
  2. filtrationThe solid was recovered by filtration
  3. additionadded to a mixture of 40 ml
  4. temperatureThe resulting mixture was heated at 100° C. for 1 hour
  5. temperaturecooled
  6. filtrationfiltered
  7. customThe residue was dried
  8. customto give 3.1 g

Sources & evidence

ORD record
ord-139f3ff2f98142efa7a0e2c763c574b2
Source dataset
uspto-grants-1987_03
Patent number
US04652658

Reaction notes

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