2-Chloro-1,3-oxazole → 4,5-Dihydro-8-methylthio-2-phenylbenzo[2,1-c:3,4-b']dithiophene-6-carboxamide

HRID 1108357Notes

Reaction equation

HRID 1108357 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]([C:21]([OH:23])=O)=[C:6]2[CH2:14][CH2:13][C:12]3[CH:11]=[C:10]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[S:9][C:8]=3[C:7]=12.O1C=C[N:26]=C1Cl>O1CCCC1.CN(C)C=O>[CH3:1][S:2][C:3]1[S:4][C:5]([C:21]([NH2:26])=[O:23])=[C:6]2[CH2:14][CH2:13][C:12]3[CH:11]=[C:10]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[S:9][C:8]=3[C:7]=12

Participants

5

Reactant 2

HCID 133710742-Chloro-1,3-oxazoleHCID 183883114,5-Dihydro-8-methylthio-2-phenylbenzo[2,1-c:3,4-b']dithiophene-6-carboxylic acid

Product 1

HCID 183883194,5-Dihydro-8-methylthio-2-phenylbenzo[2,1-c:3,4-b']dithiophene-6-carboxamideYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4,5-Dihydro-8-methylthio-2-phenylbenzo[2,1-c:3,4-b']dithiophene-6-carboxylic acid (0.50 g) was dissolved in tetrahydrofuran (10 ml); oxazolyl chloride (0.15 ml) and then N,N-dimethylformamide (one drop) were added. After the mixture was stirred at room temperature for 2 hours, it was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (30 ml); concentrated aqueous ammonia (5 ml) was added. After the reaction mixture was stirred at room temperature for one hour, it was poured over water and extracted with chloroform-methanol. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off to yield 4,5-dihydro-8-methylthio-2-phenylbenzo[2,1-c:3,4-b']dithiophene-6-carboxamide (0.28 g, 56%), which was recrystallized from ethanol. Melting point 192-193° C.

Workup

  1. concentrationit was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in tetrahydrofuran (30 ml)
  3. additionconcentrated aqueous ammonia (5 ml) was added
  4. stirringAfter the reaction mixture was stirred at room temperature for one hour
  5. additionit was poured over water
  6. extractionextracted with chloroform-methanol
  7. washThe organic layer was washed with water
  8. dry with materialdried (MgSO4)
  9. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-c8d84451e3574c5887f40154e064a772
Source dataset
uspto-grants-2000_05
Patent number
US06066658

Reaction notes

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