Acetic Acid → N-Butyl-2-thiazolamine

HRID 1643511Notes

Reaction equation

HRID 1643511 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH:7](=O)[CH2:8][CH2:9][CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[CH2:7]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 261ButanalHCID 21552-AminothiazoleHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 4712356N-Butyl-2-thiazolamine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-aminothiazole (1 g, 10 mmol) and butyraldehyde (1.44 g, 20 mmol) were mixed in dichloroethane (45 ml) and then treated with sodium triacetoxyborohydride (6 g, 28 mmol) and acetic acid (3.6 g 60 mmol). The reaction mixture was stirred at r.t. under a nitrogen atmosphere overnight. The reaction mixture then was quenched by 1N NaOH and extracted with EtOAc. The organic layer was washed with saturated NaHCO3, brine and dried over MgSO4. The solvent was evaporated to give 2-butylaminothiazole as a brown residue (1.02 g).

Workup

  1. customThe reaction mixture then was quenched by 1N NaOH
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with saturated NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d2d6e6994991450195bcbb6bf389207b
Source dataset
uspto-grants-2012_02
Patent number
US08119819B2

Reaction notes

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