Dimethylcarbamoyl Chloride → HCID 70396619, compound

HRID 1381550Notes

Reaction equation

HRID 1381550 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]#[N:13].CCN(CC)CC.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>CCO>[C:12]([CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:23]([N:22]([CH3:26])[CH3:21])=[O:24])[CH:3]=2)[NH:7][CH:6]=1)#[N:13]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 12803100HCID 12803100, compound

Product 1

HCID 70396619HCID 70396619, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7.0 g (0.041 mole) of 5-aminoindole-3-acetonitrile and 5.7 ml (0.041 mole) of Et3N in 100 ml of abs EtOH, under N2, was added 3.78 ml of dimethylcarbamyl chloride (0.041 mole). The reaction was stirred at room temperature for 24 hours. The solvent was removed in vacuo to yield a black goo (7.5 g). It was purified by dry column chromatography. Eluting it with ethylacetate first and then with 5% MeOH in EtOAc to give 3.5 g of brown solid. It was charcoaled to remove the color (MeOH as solvent). Removal of solvent gave 1.4 g of white product.

Workup

  1. customThe solvent was removed in vacuo
  2. customto yield a black goo (7.5 g)
  3. customIt was purified
  4. customby dry column chromatography
  5. washEluting it with ethylacetate first

Sources & evidence

ORD record
ord-d01593b1fb4f44768b0de1a6cfdf5a7b
Source dataset
uspto-grants-1989_02
Patent number
US04803218

Reaction notes

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