Hydrochloric Acid → HCID 13565455, compound

HRID 1589382Notes

Reaction equation

HRID 1589382 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17])=[O:7].C(N(CC)CC)C.[F:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[N:33]=[C:34]=[O:35].Cl>CS(C)=O.O>[F:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[NH:33][C:34]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]([C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[C:9]1=[O:17])=[O:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 5932582,4-Difluorophenyl isocyanateHCID 13565652HCID 13565652, compound

Product 1

HCID 13565455HCID 13565455, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 682 mg (3.0 mmole) of 3-(2-furoyl)-2-oxindole in 8 ml of dimethyl sulfoxide was added 668 mg (6.6 mmole) of triethylamine followed by 512 mg (3.3 mmole) of 2,4-difluorophenyl isocyanate. Stirring was continued for 1 hour, and then the reaction mixture was poured into 60 ml of water. The resulting mixture was acidified with 3N hydrochloric acid and then it was cooled in an ice-bath. The solid was removed by filtration and recrystallized from ca. 35 ml of acetic acid, to give 925 mg of the title compound as yellow crystals, mp 191°-192° C.

Workup

  1. temperatureit was cooled in an ice-bath
  2. customThe solid was removed by filtration
  3. customrecrystallized from ca. 35 ml of acetic acid

Sources & evidence

ORD record
ord-22d9aa5f2645475f8a62f8a9659363da
Source dataset
uspto-grants-1986_02
Patent number
US04569942

Reaction notes

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