Triethylamine → HCID 67087747, compound

HRID 2175702Notes

Reaction equation

HRID 2175702 reaction equation
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[S:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:5]=2[CH:4]=1.C(Cl)(=O)C(Cl)=O.[NH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].CCN(CC)CC.COC1C(OC)=CC2SC(C(Cl)=O)=CC=2C=1>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[S:7][C:8]([C:10]([NH:23][C:24]3[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=3[C:26]([O:28][CH3:29])=[O:27])=[O:12])=[CH:9][C:5]=2[CH:4]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 65578Oxalyl chlorideHCID 2686205,6-dimethoxy-1-benzothiophene-2-carboxylic acidHCID 85523666HCID 85523666, compound

Product 1

HCID 67087747HCID 67087747, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 5,6-dimethoxybenzo[b]thiophene-2-carboxylic acid (714 mg, 3 mmol) and DMF (20 μl) in anhydrous DCM (20 mL) was added oxalyl chloride (0.5 mL, 6 mmol) dropwise at 0° C. The mixture was then allowed to warm to room temperature and stirring was continued until the acid was consumed completely (about 1 h). The solvent was removed under reduced pressure and the crude 5,6-dimethoxybenzo[b]thiophene-2-carbonyl chloride was used directly in the next step. To a stirred solution of methyl 2-aminobenzoate (500 mg, 3.3 mmol) and Et3N (1.25 mL, 9 mmol) in anhydrous DCM (20 mL) was added 5,6-dimethoxybenzo[b]thiophene-2-carbonyl chloride in anhydrous DCM (2 mL) dropwise at 0° C. The resulting mixture was stirred at room temperature overnight. The reaction was quenched with water and extracted with DCM. The organic extract was dried over sodium sulfate, the solvent was removed under reduced pressure and the crude product was purified by re-crystallization from EtOH to give methyl 2-(5,6-dimethoxybenzo[b]thiophene-2-carboxamido)benzoate as a white solid (650 mg, 55%). LC-MS (ES-API); rt 9.38 min; m/z calculated for C19H17NO5S [M+H]+ 372.1, found 372.1.

Workup

  1. customwas consumed completely (about 1 h)
  2. customThe solvent was removed under reduced pressure
  3. stirringThe resulting mixture was stirred at room temperature overnight
  4. customThe reaction was quenched with water
  5. extractionextracted with DCM
  6. extractionThe organic extract
  7. dry with materialwas dried over sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customthe crude product was purified by re-crystallization from EtOH

Sources & evidence

ORD record
ord-f46164e4840043c48dbf70dd060b70ff
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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