Sodium Acetate → HCID 13823143, compound

HRID 649283Notes

Reaction equation

HRID 649283 reaction equation
[CH2:1]([N:6]1[CH2:11][CH2:10][CH:9]=[C:8]([C:12]2[N:13]=[C:14]([NH2:17])[S:15][CH:16]=2)[CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:18]([O-])(=[O:20])[CH3:19].[Na+]>C(OC(=O)C)(=O)C>[CH2:1]([N:6]1[CH2:11][CH2:10][CH:9]=[C:8]([C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)[CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 13823132HCID 13823132, compound

Product 1

HCID 13823143HCID 13823143, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Seven grams of the 4-(1,2,5,6-tetrahydro-1-pentyl-3-pyridinyl)-2-thiazolamine obtained in Example 6 was dissolved in 100 ml of acetic anhydride with 10 g of anhydrous sodium acetate. The solution was heated at reflux under a nitrogen atmosphere for three hours. The solvent was removed on a rotary evaporator and the residue was partitioned between 150 ml dichloromethane and 150 ml 10% sodium bicarbonate solution. The organic layer was concentrated in vacuo and the residue was chromatographed on silica gel using 2% ammonium hydroxide in ethyl acetate as the eluent. The title compound was obtained as 4.10 g of a beige solid, mp 117°-120° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux under a nitrogen atmosphere for three hours
  3. customThe solvent was removed on a rotary evaporator
  4. customthe residue was partitioned between 150 ml dichloromethane and 150 ml 10% sodium bicarbonate solution
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was chromatographed on silica gel using 2% ammonium hydroxide in ethyl acetate as the eluent

Sources & evidence

ORD record
ord-3df0c8a2a5e84e8e9ddd0f77d909c32f
Source dataset
uspto-grants-1988_04
Patent number
US04739067

Reaction notes

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