Sodium Hydroxide → HCID 67835741, compound

HRID 728172Notes

Reaction equation

HRID 728172 reaction equation
[OH-].[Na+].[ClH:3].Cl.[CH3:5][N:6]([CH2:8][C:9]1[O:13][C:12]([CH2:14][S:15][C:16](=N)N)=[CH:11][CH:10]=1)[CH3:7].BrC[C:21]1[CH:34]=[CH:33][C:24]2[N:25]=[C:26]([N:28]([CH2:31][CH3:32])C=O)[O:27][C:23]=2[CH:22]=1>O.CO.O1CCCC1>[ClH:3].[ClH:3].[CH3:7][N:6]([CH2:8][C:9]1[O:13][C:12]([CH2:14][S:15][CH2:16][C:21]2[CH:34]=[CH:33][C:24]3[N:25]=[C:26]([NH:28][CH2:31][CH3:32])[O:27][C:23]=3[CH:22]=2)=[CH:11][CH:10]=1)[CH3:5]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 12888905HCID 12888905, compoundHCID 15644570HCID 15644570, compound

Product 1

HCID 67835741HCID 67835741, compoundYield 45.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium hydroxide (464 mg) in water (4.18 ml) was added to a solution of S-(5-dimethylaminomethylfuran-2-yl)methylisothiourea dihydrochloride (1.00 g) in methanol (10 ml) and the mixture was stirred for 1 hour at ambient temperature. A solution of 6-bromomethyl-2-(N-ethylformamido)benzoxazole (1.10 g) in a mixture of methanol (20 ml) and tetrahydrofuran (5 ml) was dropwise added thereto at 0° C. and the mixture was stirred for 2 hours at the same temperature. The solvent was evaporated in vacuo. The residue was mixed with water (20 ml) and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel by eluting with chloroform-methanol (20:1, V/V). The pure base was converted to the hydrochloride in a usual manner and recrystallized from a mixture of ethanol and diisopropyl ether to give 6-[(5-dimethylaminomethylfuran 2-yl)methylthiomethyl]-2-ethylaminobenzoxazole dihydrochloride (0.33 g).

Workup

  1. additionwas dropwise added
  2. stirringat 0° C. and the mixture was stirred for 2 hours at the same temperature
  3. customThe solvent was evaporated in vacuo
  4. additionThe residue was mixed with water (20 ml)
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on silica gel
  10. washby eluting with chloroform-methanol (20:1, V/V)
  11. customrecrystallized from a mixture of ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-e9fc7afec00748b594f4d8dd6553897d
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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