Hydrochloric Acid → HCID 57541885, compound

HRID 2422281Notes

Reaction equation

HRID 2422281 reaction equation
[CH2:1]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].Cl[CH2:22][C:23]1[CH:42]=[CH:41][C:26]([CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1.Cl>CN(C)C=O>[CH2:1]([N:7]([CH2:22][C:23]1[CH:42]=[CH:41][C:26]([CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 23082815N-Hexyl-4-phenyl-2-thiazolamineHCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoate

Product 1

HCID 57541885HCID 57541885, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-hexyl-4-phenyl-1,3-thiazol-2-amine (390 mg) in N,N-dimethylformamide (1.0 mL) was added sodium hydride (60%, oil, 50 mg) at room temperature and the mixture was stirred at room temperature for 30 min. Methyl 3-(4-{[4-(chloromethyl)benzyl]oxy}phenyl)propanoate (318 mg) was added to the reaction mixture and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into 1N aqueous hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated, and the residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:19 to 1:1 by volume ratio) to give the title compound (260 mg, yield 48%) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe ethyl acetate layer was concentrated
  4. customthe residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:19 to 1:1 by volume ratio)

Sources & evidence

ORD record
ord-30e2b38ed84d4c8eaeeff2e4941aa4a8
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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