Methylamine → 6-Methoxy-N,2-dimethyl-1-benzothiophene-3-carboxamide

HRID 985187Notes

Reaction equation

HRID 985187 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](Cl)=[O:12])=[C:9]([CH3:14])[S:8][C:7]=2[CH:15]=1.[CH3:16][NH2:17]>C1COCC1>[CH3:16][NH:17][C:11]([C:10]1[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][C:7]=2[S:8][C:9]=1[CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22143646HCID 22143646, compound

Product 1

HCID 207678726-Methoxy-N,2-dimethyl-1-benzothiophene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of this crude 6-methoxy-2-methylbenzo[b]thiophene-3-carbonyl chloride in THF (50 ml) was combined with a 2.0 M solution of CH3NH2 in THF (20 ml, 40 mmole). The resultant reaction mixture was stirred at ambient temperature for 3 hours. The solvent was removed by concentration, in vacuo, and the residue obtained was partitioned between H2O (50 ml) and CH2Cl2 (50 ml). The layers were separated and the aqueous phase was extracted with CH2Cl2 (2×30 ml). The combined organic extracts were dried over Na2SO4 and concentrated, in vacuo, to give 0.8 g of an amber solid which was purified by silica gel chromatography. Elution with CH2Cl2: EtOAc (80:20) and evaporation of the appropriate fractions gave 693 mg (72%) of an off-white solid. 1H NMR (DMSO-d6) δ8.15 (1H, q, J=4.6 Hz), 7.62 (1H, d, J=8.9 Hz), 7.47 (1H, d, J=2.4 Hz), 6.97 (1H, dd, J=2.4, 8.9 Hz), 3.79 (3H, s, 2.80 (3H, d, J=4.6 Hz), 2.53 (3H, s). Anal. Calcd. for C12H13NO2S: C, 61.25; H, 5.57; N, 5.95; S, 13.63. Found: C, 60.97; H, 5.56; N, 5.85; S, 13.44.

Workup

  1. customThe resultant reaction mixture
  2. customThe solvent was removed by concentration, in vacuo
  3. customthe residue obtained
  4. customwas partitioned between H2O (50 ml) and CH2Cl2 (50 ml)
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with CH2Cl2 (2×30 ml)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-ac8a6f1434144748befab94c89cd112a
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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