Toluene → HCID 19071328, compound

HRID 1955639Notes

Reaction equation

[C:1]([CH2:3][C:4]([NH:6]CC1CCCCC1)=[O:5])#[N:2].[CH2:14]([N:18]=[C:19]=[O:20])[CH2:15][CH2:16][CH3:17].[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:14]([N:18]([CH2:27][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:19]([NH:6][C:4](=[O:5])[CH2:3][C:1]#[N:2])=[O:20])[CH2:15][CH2:16][CH3:17]

Participants

Reactant 3

HCID 1140Toluene

HCID 8110Butyl isocyanate

HCID 190713252-cyano-N-(cyclohexylmethyl)acetamide

Product 1

HCID 19071328HCID 19071328, compoundYield 30%

Procedure

2-Cyano-N-(cyclohexylmethyl)acetamide (from step (a) example 13, 7.66 g, 42.5 mmol) was also condensed with butyl isocyanate (Adrich, 7.60 ml, 63.7 mmol) in anhydrous toluene (70 mL) in a Parr bomb at 120° C. for 24 h to provide 1-butyl-3-(2-cyanoacetyl)-1-(cyclohexylmethyl)urea (3.51 g, 30%), 1H-NMR (DMSO-d6) consistent with structure. Unreacted 2-cyano-N-(cyclohexylmethyl)acetamide was also recovered (5.97 g, 70%).

Sources & evidence

ORD record: ord-98f73e69f49241b4b6a67da588bc0c7e
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05776940

Reaction notes

Loading…