Ammonium Chloride → alpha,3-Dimethyl-alpha-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol

HRID 635841Notes

Reaction equation

HRID 635841 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([C:11]2[N:18]3[C:14]([S:15][CH:16]=[C:17]3[CH3:19])=[N:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][Mg]Br.[NH4+].[Cl-]>C1COCC1>[CH3:20][C:9]([CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:11]1[N:18]2[C:14]([S:15][CH:16]=[C:17]2[CH3:19])=[N:13][CH:12]=1)[OH:10]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 57013581(2-Phenylethyl)-3-methylimidazo[2,1-b]thiazol-5-yl methanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 467106alpha,3-Dimethyl-alpha-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-Phenylethyl)-3-methylimidazo[2,1-b]thiazol-5-yl methanone (Formula B-6) (0.40 g) in THF (6 mL) was treated with 3M ethereal methyl magnesium bromide (0.6 mL) and reacted for 18 hours. The suspension was treated with 5% NH4Cl solution and precipitated α,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol (Formula B-7) was extracted into ethyl acetate. The extract was dried and evaporated to a viscous residue which deposited α,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol (Formula B-7) (0.25 g) by ether trituration. Crystallization of the filter cake from ethyl acetate gave pure α,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol (Formula B-7) (0.13 g), m.p. 131-133°.

Workup

  1. customreacted for 18 hours
  2. customprecipitated α,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol (Formula B-7)
  3. extractionwas extracted into ethyl acetate
  4. customThe extract was dried
  5. customevaporated to a viscous residue which
  6. customCrystallization of the filter cake from ethyl acetate

Sources & evidence

ORD record
ord-99497e57e05549af86d45f2c138b6d39
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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