Tert-Butylamine → HCID 13335757, compound

HRID 1583661Notes

Reaction equation

HRID 1583661 reaction equation
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][CH:5]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][CH:21]1[O:23][CH2:22]1)(=[O:3])[CH3:2].C(N1C2C=CC=CC=2SC1C1C=CC=CC=1OCC(O)C[Cl:46])(=O)C.[C:48]([NH2:52])([CH3:51])([CH3:50])[CH3:49]>C(O)C>[ClH:46].[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][CH:5]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][CH:21]([OH:23])[CH2:22][NH:52][C:48]([CH3:51])([CH3:50])[CH3:49])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 13335755HCID 13335755, compoundHCID 20255964HCID 20255964, compound

Product 1

HCID 13335757HCID 13335757, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.64 g of 3-acetyl-2-[2-(2,3-epoxypropoxy)phenyl]benzothiazoline, 1.82 g of 3-acetyl-2-[2-(3-chloro-2-hydroxypropoxy)phenyl]benzothiazoline and 10 ml of t-butylamine are dissolved in 30 ml of ethanol and the solution is refluxed for 3 hours. The solution is concentrated in vacuo, and the residue is dissolved in ethyl acetate. The solution is washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. To this solution 2N HCl/ether is added to produce crystals. Crystals are filtered to give 3.5 g (80%) of the titled compound.

Workup

  1. temperaturethe solution is refluxed for 3 hours
  2. concentrationThe solution is concentrated in vacuo
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washThe solution is washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additionTo this solution 2N HCl/ether is added
  7. customto produce crystals
  8. filtrationCrystals are filtered

Sources & evidence

ORD record
ord-7297403b1d894f84b5f9ce22ff10cc29
Source dataset
uspto-grants-1985_11
Patent number
US04552969

Reaction notes

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