Ammonia → HCID 178449126, compound

HRID 1721974Notes

Reaction equation

HRID 1721974 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:25])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:17][CH:18]=[C:19]([C:21]([O:23]C)=O)[N:20]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[NH3:26]>CO>[C:1]([NH:5][CH2:6][CH:7]([OH:25])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:17][CH:18]=[C:19]([C:21](=[O:23])[NH2:26])[N:20]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178498876HCID 178498876, compound

Product 1

HCID 178449126HCID 178449126, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-[4-(3-tert. butyl amino-2-hydroxypropoxy)phenyl]imidazole-4-carboxylate (10 g.) in methanol (100 ml.) is reacted in a bomb with ammonia (44 g.) at 100° C. for about 24 hours. The reaction mixture is concentrated under reduced pressure and the residue is chromatographed on silica gel. The product is eluted with chloroform that is washed with concentrated aqueous ammonia (90%) and methanol (10%) and is recrystallized from acetonitrile to yield the 2-[4-(3-tert. butylamino-2-hydroxypropoxy)phenyl]-4-carbamoylimidazole as a white solid, m.p. 149°-154° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue is chromatographed on silica gel
  3. washThe product is eluted with chloroform that
  4. washis washed with concentrated aqueous ammonia (90%) and methanol (10%)
  5. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-08ccab4c7f3546cf880f24d6bc9f5b77
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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