Butyl isocyanate → HCID 178449847, compound

HRID 614343Notes

Reaction equation

HRID 614343 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[NH:12][C:11]3=[O:19])=[CH:4][C:3]=2[O:2]1.[CH2:20]([N:24]=[C:25]=[O:26])[CH2:21][CH2:22][CH3:23].C1OC2C=CC(N3C4=NC=CC=C4NC3=O)=CC=2[O:28]1.C(C(N)=O)CCC>C(COC)OC>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[NH:12][C:11]3=[O:19])=[CH:4][C:3]=2[O:2]1.[CH2:20]([N-:24][C:25]([OH:28])=[O:26])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 119617392H-Imidazo[4,5-b]pyridin-2-one, 3-(1,3-benzodioxol-5-yl)-1,3-dihydro-HCID 131711457HCID 131711457, compound

Product 1

HCID 178449847HCID 178449847, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of 1.2 g. of 1,3-dihydro-3-(3,4-methylenedioxyphenyl)imidazo[4,5-b]pyridin-2-one in 75 ml. of dry dimethoxyethane was treated with 1 g. of n-butyl isocyanate and refluxed until solution was complete. The solution was filtered and evaporated to near dryness and diluted with petroleum ether. The precipitate was recrystallized from 30 ml. of ethanol by addition of water to give 400 mg. of 1,3-dihydro-3-(3,4-methylenedioxyphenyl)-2-oxoimidazo[4,5-b]pyridine-1-n-butylcarboxamide,. m.p. 129°-130° C.

Workup

  1. additionA suspension of 1.2 g
  2. filtrationThe solution was filtered
  3. customevaporated
  4. additiondiluted with petroleum ether
  5. customThe precipitate was recrystallized from 30 ml
  6. additionof ethanol by addition of water
  7. customto give 400 mg

Sources & evidence

ORD record
ord-4c0556a970b14a9f9ae67bf663002da8
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

Loading…