Dimethylformamide → HCID 86758626, compound

HRID 2296812Notes

Reaction equation

HRID 2296812 reaction equation
[CH2:1]([C:3]1[S:4][C:5]2[CH2:11][CH2:10][C:9]3=[C:12]([C:17]([OH:19])=O)[S:13][C:14]([S:15][CH3:16])=[C:8]3[C:6]=2[N:7]=1)[CH3:2].C(Cl)(=O)C(Cl)=O.C[N:27](C)C=O>O1CCCC1>[CH2:1]([C:3]1[S:4][C:5]2[CH2:11][CH2:10][C:9]3=[C:12]([C:17]([NH2:27])=[O:19])[S:13][C:14]([S:15][CH3:16])=[C:8]3[C:6]=2[N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 18388314HCID 18388314, compound

Product 1

HCID 86758626HCID 86758626, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Ethyl-4,5-dihydro-8-methylthiothieno[3,4-e]benzothiazole-6-carboxylic acid (0.47 g) was suspended in tetrahydrofuran (15 ml); oxalyl chloride (0.29 g) and then N,N-dimethylformamide (6 l) 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 (8 ml); this suspension was added to a solution of diethyl 4-aminobenzylphosphonate (0.40 g), triethylamine (0.17 g) and tetrahydrofuran (15 ml) at room temperature. 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 1 N hydrochloric acid, water, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4), after which the solvent was distilled off to yield N-[4-]diethoxyphosphorylmethyl)phenyl]-2-ethyl-4,5-dihydro-8-methylthiothieno[3,4-e]benzothiazole-6-carboxamide (0.69 g, 85%), which was then recrystallized from ethanol-hexane. Yellow needles. Melting point 179-180° C.

Workup

  1. concentrationit was concentrated under reduced pressure
  2. additionthis suspension was added to a solution of diethyl 4-aminobenzylphosphonate (0.40 g), triethylamine (0.17 g) and tetrahydrofuran (15 ml) at room temperature
  3. stirringAfter the reaction mixture was stirred at room temperature for 1 hour
  4. additionit was poured over water (150 ml)
  5. extractionextracted with ethyl acetate-tetrahydrofuran (3:1
  6. washThe organic layer was washed with 1 N hydrochloric acid, water
  7. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4)
  8. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-a13b2912d2734e5d87e741e3cceca70c
Source dataset
uspto-grants-2002_12
Patent number
US06489351B1

Reaction notes

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