Ethyl isocyanate → HCID 16050215, compound

HRID 2267080Notes

Reaction equation

HRID 2267080 reaction equation
[CH3:1][N:2]([CH3:39])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([C@@H:9]1[CH2:23][C@H:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[N:16]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:15]=3)[N:11]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:10]1)=[O:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:59]([N:61]=[C:62]=[O:63])[CH3:60]>ClCCl.[Cu]Cl>[CH3:39][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]([C:62]([NH:61][CH2:59][CH3:60])=[O:63])[C:7]([C@@H:9]1[CH2:23][C@H:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[N:16]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:15]=3)[N:11]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:10]1)=[O:8]

Participants

6

Reactant 3

HCID 8022Ethyl isocyanateHCID 11776TriphenylphosphineHCID 86617040HCID 86617040, compound

Product 1

HCID 16050215HCID 16050215, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 15.5 g (28.67 mmol) of N-[3-(dimethylamino)propyl]-1,6-di(tert-butoxycarbonyl)-ergoline-8β-carboxamide (XVII, R2=tert-butyl) in 350 ml of dichloro-methane 0.8 g of triphenylphosphine, 0.3 g of copper(I) chloride and 6.8 ml (86 mmol) of ethyl isocyanate was sequentially added, and the reaction mixture was stirred at 35° C. for 4 hours. The reaction mixture was concentrated in vacuum and the product was purified on a silica plug to give 16.9 g (96.4%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum
  2. customthe product was purified on a silica plug

Sources & evidence

ORD record
ord-c25f2f2b3c574cc9b3b7f9e8d75e5831
Source dataset
uspto-grants-2010_12
Patent number
US07858791B2

Reaction notes

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