Allyl isocyanate → HCID 15027399, compound

HRID 1195895Notes

Reaction equation

HRID 1195895 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][NH:20][OH:21])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1.[CH2:25]([N:28]=[C:29]=[O:30])[CH:26]=[CH2:27].C([O-])(=O)C.[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][N:20]([OH:21])[C:29]([NH:28][CH2:25][CH:26]=[CH2:27])=[O:30])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 15123Allyl isocyanateHCID 517045Sodium AcetateHCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

Product 1

HCID 15027399HCID 15027399, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

According to the procedure of Example 62, 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine is reacted with 1.2 eq of allyl isocyanate in dioxane/water (1:1) in the presence of sodium acetate (2.5 eq). The crude product is purified by column chromatography (silica, 3:7 ethyl acetate:methylene chloride). Recrystallization from methylene chloride:hexane, and then from methanol:water gives pure 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-N-[(2-propenylamino) carbonyl]-1H-indole-3-methanamine (44%); mp 148°-149° C.

Workup

  1. customThe crude product is purified by column chromatography (silica, 3:7 ethyl acetate:methylene chloride)
  2. customRecrystallization from methylene chloride

Sources & evidence

ORD record
ord-ba1fc873ca944af181a20ae6d722251f
Source dataset
uspto-grants-1992_05
Patent number
US05112846

Reaction notes

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