Triethylamine → HCID 13560792, compound

HRID 1285509Notes

Reaction equation

HRID 1285509 reaction equation
[C:1]1([CH:7]2[S:18][CH:10]3[S:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N:9]3[C:8]2=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([OH:24])=[O:23].C(N(CC)CC)C>C(Cl)Cl>[S:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:9]=[C:10]1[S:18][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([N:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([OH:24])=[O:23])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 145742L-ProlineHCID 20249371HCID 20249371, compound

Product 1

HCID 13560792HCID 13560792, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.7 g (0.02 m) 2-phenylthiazolo[2,3-b]benzothiazol-3(2H)-one mesoionic didehydro derivative, 2.2 g (0.02 m)-L-(-)-proline and 2.0 g (0.02 m) triethylamine are suspended in methylene chloride and the mixture is stirred at room temperature overnight. The reaction mixture is extracted with a dilute hydrochloric acid solution and dried over anhydrous magnesium sulfate. After the solvent is removed, the residue is extracted with hot cyclohexane. The solid obtained from the cyclohexane solution is recrystallized from acetonitrile. In order to remove all traces of acetonitrile, the solid is ground, stirred in water for 3 days, collected and then dried in an oven at 90° C. There is thereby obtained 3.0 g (37% yield) of the title compound, which has a melting point of 174°-5° C. (dec).

Workup

  1. extractionThe reaction mixture is extracted with a dilute hydrochloric acid solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter the solvent is removed
  4. extractionthe residue is extracted with hot cyclohexane
  5. customThe solid obtained from the cyclohexane solution
  6. customis recrystallized from acetonitrile
  7. customIn order to remove all traces of acetonitrile
  8. stirringstirred in water for 3 days
  9. customcollected
  10. customdried in an oven at 90° C

Sources & evidence

ORD record
ord-07579fb39f964f428666bf691a308032
Source dataset
uspto-grants-1986_01
Patent number
US04567267

Reaction notes

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