Sodium Hydroxide → HCID 9838514, compound

HRID 1655809Notes

Reaction equation

HRID 1655809 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[BH4-].[Na+].O[N:9]=[CH:10][C:11]1[S:15][C:14]([C:16]2[S:17][C:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[CH:19][CH:20]=2)=[CH:13][CH:12]=1.[OH-].[Na+]>O.COCCOC>[NH2:9][CH2:10][C:11]1[S:15][C:14]([C:16]2[S:17][C:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[CH:19][CH:20]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 4311764Sodium borohydrideHCID 85624266HCID 85624266, compound

Product 1

HCID 9838514HCID 9838514, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A volume of 1.65 ml tin(IV)chloride and 0.76 g of sodium borohydride are added at 0° C. to 30 ml of 1,2-dimethoxyethane. The above-obtained oxime in a quantity of 1.5 g is added portion-wise to the above mixture, after which the reaction mixture is stirred overnight at room temperature. Then a mixture of water and a 2N NaOH solution is added while cooling on ice, after which the product is extracted with ethyl acetate. The ethyl acetate layer is treated with 2N hydrochloric acid and the product is filtered. The desired 5-aminomethyl-2,2':5',2''-terthiophene (1) is obtained, after drying, in a yield of 0.6 g; UV-abs. spectrum: λmax =355 nm, γ=20,000.

Workup

  1. temperaturewhile cooling on ice
  2. extractionafter which the product is extracted with ethyl acetate
  3. additionThe ethyl acetate layer is treated with 2N hydrochloric acid
  4. filtrationthe product is filtered

Sources & evidence

ORD record
ord-171346b075374fb3ae8747d0cbb7e81f
Source dataset
uspto-grants-1993_10
Patent number
US05252191

Reaction notes

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