Isobutyl chloroformate → HCID 131715971, compound

HRID 1904774Notes

Reaction equation

HRID 1904774 reaction equation
[Cl:1][C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[NH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][C:20]#[N:21]>CN(C=O)C.O>[ClH:1].[NH2:21][CH2:20][CH2:19][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([NH:9][C:2](=[O:3])[O:4][CH2:5][CH:6]([CH3:8])[CH3:7])[CH:11]=2)[NH:15][CH:14]=1

Participants

5

Reactant 2

HCID 62365Isobutyl chloroformateHCID 12803100HCID 12803100, compound

Product 1

HCID 131715971HCID 131715971, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Isobutyl chloroformate (1.5 ml) was added dropwise to a stirred solution of 5-amino-1H-indole-3-acetonitrile (1.7 g) in dry DMF (20 ml). After 10 min the solution was diluted with water (150 ml) and stirring continued for 30 min. The resulting solution was extracted with ethyl acetate (2×100 ml) and the combined extracts washed with brine (10%, 100 ml), water (100 ml), dried (Na2SO4) and evaporated in vacuo to yield the crude product as a brown oil. This was purified by column chromatography (Kieselgel 60, 100 g) using ether as the eluent, to give the title compound as a colourless gum (1.08 g) which darkened to a brown gum on storage. This material failed to crystallise from common organic solvents.

Workup

  1. extractionThe resulting solution was extracted with ethyl acetate (2×100 ml)
  2. washthe combined extracts washed with brine (10%, 100 ml), water (100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customto yield the crude product as a brown oil
  6. customThis was purified by column chromatography (Kieselgel 60, 100 g)

Sources & evidence

ORD record
ord-de80e1a5fe814a7c818100bd32da2a5b
Source dataset
uspto-grants-1989_06
Patent number
US04839377

Reaction notes

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