Hydrochloric Acid → 1-(2-Fluoro-4-biphenylyl)ethyl-2-dimethylaminothiazole

HRID 974044Notes

Reaction equation

HRID 974044 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[N:11]=[C:12]([NH:15][CH3:16])[S:13][CH:14]=2)[CH3:9])[CH:5]=[CH:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CI.[CH2:25]([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].Cl>C1C=CC=CC=1.O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[N:11]=[C:12]([N:15]([CH3:25])[CH3:16])[S:13][CH:14]=2)[CH3:9])[CH:5]=[CH:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 16028TetrabutylammoniumHCID 1242384-(1-(2-Fluoro-4-biphenyl)ethyl)-2-methylaminothiazole

Product 1

HCID 156760211-(2-Fluoro-4-biphenylyl)ethyl-2-dimethylaminothiazoleYield 85%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylaminothiazole(415 mg, 1.33 mmol) in benzene (6 ml) was added methyl iodide (370 mg, 2.61 mmol), tetra-n-butyl ammonium hydrogene sulfate (435 mg, 1.33 mmol) and 50% NaOH aq. (3 ml), then the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water, then acidified with 2N-HCl to pH 6 and the aqueous solution was extracted with benzene. The extracts were washed with water, dried and then evaporated under reduced pressure to a residue, which chromatographed to afford 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-dimethylaminothiazole (369 mg, 85% yield): NMR(CDCl3)δ 1.62(d, 3H), 3.06(s, 6H), 4.09(q, 1H), 6.06(s, 1H), 7.02-7.63(m, 8H) ppm; IR(neat) 2950, 1620, 1550, 1420, 1340 cm-1.

Workup

  1. extractionthe aqueous solution was extracted with benzene
  2. washThe extracts were washed with water
  3. customdried
  4. customevaporated under reduced pressure to a residue, which
  5. customchromatographed

Sources & evidence

ORD record
ord-e391e34c56674ed4a8cb783ceb4b593c
Source dataset
uspto-grants-1991_11
Patent number
US05066666

Reaction notes

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