MAGNESIUM SILICATE (synthetic) → HCID 15617183, compound

HRID 2073114Notes

Reaction equation

HRID 2073114 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[C:10]([NH:15][CH2:16][CH:17]([OH:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:11][CH:12]=[CH:13][CH:14]=2)=O)=[CH:4][CH:3]=1.[O-][Si]([O-])=O.[Mg+2]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]2[N:15]([CH2:16][CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[OH:24])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 15617228HCID 15617228, compound

Product 1

HCID 15617183HCID 15617183, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-N-[2-[(2-hydroxy-2-phenylethyl)amino]-3-pyridinyl]benzamide (13.2 g, 0.036 mole) was heated at 180°-190° C. in a glass flask on a Wood's metal bath for 12 minutes. The residue was dissolved in ethyl acetate, treated with Florisil®, and filtered. The filtrate was diluted with hexanes to initiate crystallization. The solid was collected by filtration, washed with ethyl acetate/hexanes mixture and then hexane. The solid still contained 10-15% uncyclized material, and therefore a portion of the solid (1.25 g) was heated at 180°-190° C. for an additional 17 minutes. The solid residue was recrystallized from methylene chloride/hexane and dried under high vacuum at 70° C. overnight to give 0.8 g of solid, mp. 166°-168° C.

Workup

  1. filtrationfiltered
  2. additionThe filtrate was diluted with hexanes
  3. customcrystallization
  4. filtrationThe solid was collected by filtration
  5. washwashed with ethyl acetate/hexanes mixture
  6. temperatureThe solid still contained 10-15% uncyclized material, and therefore a portion of the solid (1.25 g) was heated at 180°-190° C. for an additional 17 minutes
  7. customThe solid residue was recrystallized from methylene chloride/hexane
  8. customdried under high vacuum at 70° C. overnight

Sources & evidence

ORD record
ord-c5af543fa74a47bb8026997584c5248f
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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