Ammonia → HCID 178479630, compound

HRID 893968Notes

Reaction equation

HRID 893968 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[N:6]=[C:5]([OH:14])[CH:4]=1.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[CH:23]([OH:30])[CH2:24][N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1.[OH-].[Na+].Cl.N>O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CCOCC.O1CCCC1>[ClH:13].[Cl:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[C:5]([OH:14])[CH:4]=[C:3]2[CH2:2][O:30][CH:23]([C:17]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=1[Cl:15])[CH2:24][N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

10

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 178515813HCID 178515813, compound

Product 1

HCID 178479630HCID 178479630, compound

Reagents, catalysts & solvents 4

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent3×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.1 g of 4-bromomethyl-6-chloro-2-hydroxyquinoline (0.015 mol), 3.9 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.015 mol), 15.2 g of sodium hydroxide (0.38 mol) in 15 ml of water, 0.25 g of benzyltrimethylammonium chloride and 50 ml of tetrahydrofuran are reacted in a manner similar to the procedure of Example 1. After work up of the mixture, the oily product is treated with water and ether. To the aqueous layer is added half concentrated hydrochloric acid (pH 5) and subsequently aqueous ammonia (10%) for neutralization of the hydrochloride. The deposited oily product is extracted with chloroform and the chloroform layer is washed with water, dried and charcoaled. Then the solvent is removed in vacuo, the solid product dissolved in ethyl acetate and to the clear solution is added etheral hydrochloric acid. The precipitated hydrochloride (3.4 g) is washed with ethyl acetate, treated with boiling acetonitrile and then with anhydrous ether. The filtered off product, which contains two moles of crystal water, is dried at 70°-75° C.; m.p. 176°-178° C.

Workup

  1. extractionThe deposited oily product is extracted with chloroform
  2. washthe chloroform layer is washed with water
  3. customdried
  4. customThen the solvent is removed in vacuo
  5. dissolutionthe solid product dissolved in ethyl acetate and to the clear solution
  6. additionis added etheral hydrochloric acid
  7. washThe precipitated hydrochloride (3.4 g) is washed with ethyl acetate
  8. additiontreated with boiling acetonitrile
  9. filtrationThe filtered off product, which
  10. customis dried at 70°-75° C.

Sources & evidence

ORD record
ord-0ed0cbeef85f4d51bd6322613f2b276c
Source dataset
uspto-grants-1981_08
Patent number
US04282230

Reaction notes

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