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

HRID 616794Notes

Reaction equation

HRID 616794 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-04c5c243812f4596a44f25b322663953
Source dataset
uspto-grants-1978_02
Patent number
US04075224

Reaction notes

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