Hydrochloric Acid → HCID 18174778, compound

HRID 747437Notes

Reaction equation

HRID 747437 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:28]3[CH:32]=[CH:31][N:30]=[C:29]3[CH3:33])[O:11][C:12]=2[CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20](CC([O-])=O)=[CH:19][C:18]=2[CH3:27])=[CH:4][CH:3]=1.Cl.C[OH:36]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:28]3[CH:32]=[CH:31][N:30]=[C:29]3[CH3:33])[O:11][C:12]=2[CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([OH:36])=[CH:19][C:18]=2[CH3:27])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 18174770HCID 18174770, compound

Product 1

HCID 18174778HCID 18174778, compoundYield 99%

Procedure

A mixture of [4-[3-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]propyloxy]-3-methylphenyl]acetate (4.30 g), 37% hydrochloride (3 ml), and methanol (150 ml) was stirred at room temperature for 1 hour. The reaction mixture was concentrated, which was poured into a 10% aqueous solution of sodium hydrogen carbonate. The precipitated crystals were filtered, washed with pure water and air-dried to give crystals of 4-[3-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]propyloxy]-3-methylphenol (3.90 g, 99%). Recrystallization from tetrahydrofuran-hexane gave colorless prisms (2.56 g, 65%). Melting point 175-176° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwhich was poured into a 10% aqueous solution of sodium hydrogen carbonate
  3. filtrationThe precipitated crystals were filtered
  4. washwashed with pure water
  5. customair-dried

Sources & evidence

ORD record
ord-bc75a64b6d694a5790b46d407499fb9e
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Reaction notes

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