Ammonia → HCID 136387283, compound

HRID 638026Notes

Reaction equation

HRID 638026 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10]=[C:9]1[C:17]1[O:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=2)=[CH:20][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC(C(O)=O)CCSC.N>CS(O)(=O)=O>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10]=[C:9]1[C:17]1[O:18][C:19]([C:22]2[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=2)=[CH:20][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 876(+-)-MethionineHCID 20255155HCID 20255155, compound

Product 1

HCID 136387283HCID 136387283, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 19.6 g of 2-[1-benzyl-4-(trifluoromethyl)-imidazol-2-yl]-5-(4-methoxyphenyl)-furan and 8.1 g of D,L-methionine in 110 ml of methanesulphonic acid is stirred under nitrogen for 20 hours at 100°. After cooling, the reaction mixture is poured onto ice, the pH is adjusted to 8 with concentrated ammonia and the mixture is extracted several times with methylene chloride. Washing with water, drying and concentration by evaporation of the organic phase yield the crystalline 2-[1-benzyl-4-(trifluoromethyl)-1H-imidazol-2-yl]-5-(4-hydroxyphenyl)-furan which is used as such in the next step.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture is poured onto ice
  3. extractionthe mixture is extracted several times with methylene chloride
  4. washWashing with water
  5. customdrying
  6. concentrationconcentration
  7. customby evaporation of the organic phase

Sources & evidence

ORD record
ord-125d4c1a62ed456880d121d3b9f4db40
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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