2-Methylindole → 5-(2-methyl-3-indolyl)-5-(1-ethyl-2-methyl-3-indolyl)3,4-dichloro-2(5H)-furanone

HRID 1680790Notes

Reaction equation

HRID 1680790 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](=O)[C:13]([Cl:19])=[C:14]([Cl:18])[C:15]([OH:17])=[O:16])=[C:4]1[CH3:21])[CH3:2].[CH3:22][C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2>C(OC(=O)C)(=O)C>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2([C:31]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][C:23]=3[CH3:22])[O:17][C:15](=[O:16])[C:14]([Cl:18])=[C:13]2[Cl:19])=[C:4]1[CH3:21])[CH3:2]

Participants

4

Reactant 2

HCID 72242-MethylindoleHCID 545093234-(1-Ethyl-2-methyl-3-indolyl)-2,3-dichloro-4-oxo-2-butenoic acid

Product 1

HCID 204427125-(2-methyl-3-indolyl)-5-(1-ethyl-2-methyl-3-indolyl)3,4-dichloro-2(5H)-furanone

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 10.0 g (0.047 mole) of 4-(1-ethyl-2-methyl-3-indolyl)-2,3-dichloro-4-oxo-2-butenoic acid, 4.0 g (0.030 mole) of 2-methylindole and 150 ml of acetic anhydride was stirred at ambient temperature in an atmosphere of air for approximately seventeen hours and the solid which formed was collected by filtration. After drying in vacuo at 60° C. there was obtained 5-(1-ethyl-2-methyl-3-indolyl)-5-(2-methyl-3-indolyl)-3,4-dichloro-2(5H)-furanone (Formula V: R=CH3CH2 ; R1 =R3 =CH3 ; R2 =Y=Y1 =H) as a blue-colored solid which melted over the range of 282°-285° C.

Workup

  1. customthe solid which formed
  2. filtrationwas collected by filtration
  3. customAfter drying in vacuo at 60° C.

Sources & evidence

ORD record
ord-64a0b35d82344ef4bea6fb96f73c01be
Source dataset
uspto-grants-1981_06
Patent number
US04275121

Reaction notes

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