Urea → HCID 53739905, compound

HRID 436757Notes

Reaction equation

HRID 436757 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].[N:6]([C:17]([N:23]=[C:24]=[O:25])([CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:18])=[N:7][C:8]([N:14]=[C:15]=[O:16])([CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:9].N[C:27]([NH2:29])=O.[N-]=C=O.[CH3:33][CH2:34][CH2:35]CC>>[N:6]([C:17]([NH:23][C:24]([NH:29][CH2:27][CH:34]([CH3:35])[CH3:33])=[O:25])([CH2:19][CH:20]([CH3:21])[CH3:22])[CH3:18])=[N:7][C:8]([NH:14][C:15]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:16])([CH2:10][CH:11]([CH3:12])[CH3:13])[CH3:9]

Participants

6

Reactant 5

HCID 1176UreaHCID 6558IsobutylamineHCID 8003Pentane2×HCID 105034IsocyanateHCID 54086705HCID 54086705, compound

Product 1

HCID 53739905HCID 53739905, compound

Procedure

To a solution of 3.44 grams (0.047 moles) of isobutylamine in 20 ml of pentane in a 50 ml erlenmeyer flask, cooled by a water bath, was added dropwise with stirring 6.56 grams (0.0235 moles) of 2,2'-azobis(2-isocyanato-4-methylpentane) (from Example XXIX). The reaction was stirred for 90 minutes during which time the insoluble product dropped out of the pentane. The pentane was evaporated under reduced pressure leaving 5.9 grams (59% crude yield) of a viscous light brown liquid. The infrared spectrum of the product showed a strong broad urea type carbonyl at 1610 cm-1. The isocyanate band at 2250 cm-1 that was present in the starting material is absent.

Workup

  1. additionwas added dropwise
  2. customThe pentane was evaporated under reduced pressure
  3. customleaving 5.9 grams (59% crude yield) of a viscous light brown liquid

Sources & evidence

ORD record
ord-9bef2cb4828b4dada87815eb39b8ddfb
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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