Ammonia → HCID 178449126, compound

HRID 325347Notes

Reaction equation

HRID 325347 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. butylamino-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 24 hours. The reaction mixture is concentrated under reduced pressure and the residue is chromatographed on silica gel. The product is eluted with cloroform 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 cloroform that
  4. washis washed with concentrated aqueous ammonia (90%) and methanol (10%)
  5. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c947f281ab684df6ad24b27d2b1c6ba8
Source dataset
uspto-grants-1984_04
Patent number
US04440774

Reaction notes

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