Dimethylformamide → N-ethyl-4,5-dihydro-8-methylthio-2-phenylthieno[3,4-e]benzothiazole-6-carboxamide

HRID 1936879Notes

Reaction equation

HRID 1936879 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]([C:21](O)=[O:22])=[C:6]2[C:20]=1[C:10]1[N:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:13][C:9]=1[CH2:8][CH2:7]2.[C:24](Cl)(=O)[C:25](Cl)=O.C[N:31](C)C=O>O1CCCC1>[CH2:24]([NH:31][C:21]([C:5]1[S:4][C:3]([S:2][CH3:1])=[C:20]2[C:10]3[N:11]=[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[S:13][C:9]=3[CH2:8][CH2:7][C:6]=12)=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 120435044,5-Dihydro-8-methylthio-2-phenylthieno[3,4-e]benzothiazole-6-carboxylic acid

Product 1

HCID 12043512N-ethyl-4,5-dihydro-8-methylthio-2-phenylthieno[3,4-e]benzothiazole-6-carboxamideYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,5-Dihydro-8-methylthio-2-phenylthieno[3,4-e]benzothiazole-6-carboxylic acid (0.43 g) was suspended in tetrahydrofuran (15 ml); oxalyl chloride (0.23 g) and then N,N-dimethylformamide (6 μl) were added. After this mixture was stirred at room temperature for 2 hours, it was concentrated under reduced pressure. The residue was suspended in tetrahydrofuran (5 ml) and cooled with ice; a 70% aqueous solution of ethylamine (4.0 ml) was added. After the reaction mixture was stirred at room temperature for 1 hour, it was poured over water (150 ml) and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off to yield N-ethyl-4,5-dihydro-8-methylthio-2-phenylthieno[3,4-e]benzothiazole-6-carboxamide (0.35 g, 76%), which was then recrystallized from chloroform-ethanol. Yellow needles. Melting point 211-212° C.

Workup

  1. concentrationit was concentrated under reduced pressure
  2. temperaturecooled with ice
  3. additiona 70% aqueous solution of ethylamine (4.0 ml) was added
  4. stirringAfter the reaction mixture was stirred at room temperature for 1 hour
  5. additionit was poured over water (150 ml)
  6. extractionextracted with ethyl acetate-tetrahydrofuran (3:1
  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-d86c94702e1f44c59b640f0b94fcfc77
Source dataset
uspto-grants-2002_05
Patent number
US06391905B1

Reaction notes

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