Ammonia → HCID 136018549, compound

HRID 638053Notes

Reaction equation

HRID 638053 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]1[C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=1.NC(C(O)=O)CCSC.N>CS(O)(=O)=O>[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]([F:11])([F:10])[F:12])[N:6]=[C:5]1[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 876(+-)-MethionineHCID 20255117HCID 20255117, compound

Product 1

HCID 136018549HCID 136018549, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 14.6 g of 1-(2-hydroxyethyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1H-imidazole and 8.7 g of DL-methionine in 90 ml of methanesulphonic acid is stirred for 24 hours at 110°, then cooled, poured onto ice and the pH is adjusted to 10 with ammonia. The mixture is extracted several times with ethyl acetate, the combined organic phases are dried over sodium sulphate, filtered and the filtrate is concentrated to a small volume. 1-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-4-(trifluoromethyl)-1H-imidazole having a melting point of 186°-188° can be obtained in crystalline form by the addition of hexane.

Workup

  1. temperaturecooled
  2. additionpoured onto ice
  3. extractionThe mixture is extracted several times with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to a small volume

Sources & evidence

ORD record
ord-238af916d68c4469a5888adcd3fd9ccf
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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