Water → HCID 21269994, compound

HRID 1194380Notes

Reaction equation

HRID 1194380 reaction equation
[CH3:1][Mg]I.[Cl:4][C:5]1[CH:14]=[C:13]([C:15]([C:17]2[N:18]=[CH:19][N:20]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=2)=[O:16])[C:8]2[O:9][CH2:10][O:11][CH2:12][C:7]=2[CH:6]=1.[Cl-].[NH4+].O>C(OCC)C.O1CCCC1>[Cl:4][C:5]1[CH:14]=[C:13]([C:15]([CH3:1])([C:17]2[N:18]=[CH:19][N:20]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=2)[OH:16])[C:8]2[O:9][CH2:10][O:11][CH2:12][C:7]=2[CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 21269991HCID 21269991, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 21269994HCID 21269994, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 0.148 mole of methyl magnesium iodide in 150 ml of diethyl ether at a temperature of 30° C., is added at ambient temperature to 17.3 g (0.033 mole) of (6-chloro-4H-1,3-benzodioxin-8-yl)(1-triphenylmethyl-1H-imidazol-4-yl)ketone dissolved in 200 ml of tetrahydrofuran. The temperature of the reaction mixture increases to 40° C. When the addition is complete, stirring is maintained for 1 hour at ambient temperature. There is then added 8 g of ammonium chloride and stirring is continued for a further hour. Subsequently, 100 ml of water are added and the reaction mixture is extracted twice with dichloromethane. The organic phases are dried over anhydrous sodium sulfate and the solvent is removed under reduced pressure. The residue is recrystallized from 100 ml of ethyl acetate. 13.77 g of alpha-(6-chloro-4H-1,3-benzodioxin-8-yl)-alpha-methyl-1-triphenylmethyl-1H-imidazole-4-methanol are obtained. Yield: 80% of theory; M.P.: 248°-250° C. (decomposition).

Workup

  1. additionWhen the addition
  2. temperatureis maintained for 1 hour at ambient temperature
  3. stirringstirring
  4. waitis continued for a further hour
  5. extractionthe reaction mixture is extracted twice with dichloromethane
  6. dry with materialThe organic phases are dried over anhydrous sodium sulfate
  7. customthe solvent is removed under reduced pressure
  8. customThe residue is recrystallized from 100 ml of ethyl acetate

Sources & evidence

ORD record
ord-bf9f9519e7fa41fe904c473c609bf98b
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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