Diethyl Ether → HCID 131715970, compound

HRID 1904768Notes

Reaction equation

HRID 1904768 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].CN[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][C:19]#[N:20].CCOCC.[CH3:26][N:27](C)C=O>O>[C:19]([CH2:18][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([CH2:26][NH:27][C:2](=[O:3])[O:4][CH2:5][CH3:6])[CH:10]=2)[NH:14][CH:13]=1)#[N:20]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 10928Ethyl chloroformateHCID 12803103HCID 12803103, compound

Product 1

HCID 131715970HCID 131715970, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl chloroformate (0.21 ml) was added dropwise to a stirred solution of 5-(methylamino)-1H-indole-3-acetonitrile (0.4 g) in dimethylformamide (15 ml). After 10 min. the solution was diluted with water (30 ml), stirred for 30 min. and extracted with ethyl acetate (2×100 ml). The combined extracts were washed with 10% brine (2×100 ml), 8% sodium bicarbonate (2×100 ml) and water (2×100 ml), dried (Na2SO4) and evaporated in vacuo to yield the crude product as a brown oil. Trituration with ether gave a fawn solid (0.4 g). A sample was crystallised from ether to give the title compound as a white solid m.p. 104°-106°.

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe combined extracts were washed with 10% brine (2×100 ml), 8% sodium bicarbonate (2×100 ml) and water (2×100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customto yield the crude product as a brown oil

Sources & evidence

ORD record
ord-714b78d7caa74669a7d137ea463baea2
Source dataset
uspto-grants-1989_06
Patent number
US04839377

Reaction notes

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