Butyl isocyanate → HCID 13732385, compound

HRID 648483Notes

Reaction equation

HRID 648483 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]([O:15]CC)=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N:18]([CH2:21][CH2:22][CH2:23][CH3:24])=[C:19]=[O:20]>CN(C)C1C=CN=CC=1.ClC(Cl)Cl>[CH2:21]([N:18]1[C:13](=[O:15])[CH2:12][N:11]([C:8]2[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:10][CH:9]=2)[C:19]1=[O:20])[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 8110Butyl isocyanateHCID 13732399HCID 13732399, compound

Product 1

HCID 13732385HCID 13732385, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 25 parts of ethyl 2-[[4-(acetylamino)phenyl]amino]acetate, 20 parts of 1-isocyanatobutane, 2 parts of N,N-dimethyl-4-pyridinamine and 300 parts of trichloromethane was stirred and refluxed for 48 hours. The reaction mixture was evaporated and the residue was stirred and refluxed for 8 hours in 180 parts of dimethylbenzene. After cooling, the precipitated product was filtered off, washed with 2-propanol and dried, yielding 25.5 parts (83%) of N-[4-(3-butyl-2,4-dioxo-1-imidazolidinyl)phenyl]acetamide; mp. 192.8° C. (13).

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe reaction mixture was evaporated
  3. stirringthe residue was stirred
  4. temperaturerefluxed for 8 hours in 180 parts of dimethylbenzene
  5. temperatureAfter cooling
  6. filtrationthe precipitated product was filtered off
  7. washwashed with 2-propanol
  8. customdried

Sources & evidence

ORD record
ord-32d03e2c57bb4943b356dab4abc5ae6e
Source dataset
uspto-grants-1988_04
Patent number
US04735942

Reaction notes

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