Triethylamine → 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene-3-carbonitrile

HRID 850729Notes

Reaction equation

HRID 850729 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([NH2:13])=O)=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[S:8][C:7]=2[CH:22]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]#[N:13])=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[S:8][C:7]=2[CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 154582696-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamide

Product 1

HCID 154582706-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene-3-carbonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamide (0.4488 g, 1.43 mmol) in tetrahydrofuran (20 ml) at 5° C. is added triethylamine (0.5 ml, 3.58 mmol) and trifluoroacetic acid anhydride (0.26 ml, 1.79 mmol). The cooling bath is removed and the reaction allowed to warm to room temperature and stir for 16 hours. The contents are partitioned between water and methylene chloride, and the organic layer is separated, dried over magnesium sulfate, filtered and concentrated to a solid, which is chromatographed on silica gel (9:1 dichloromethane:toluene) to afford 386.9 mg (92%) of title compound as a solid: mp 141.7-142.9° C. IR (KBr) 2985, 2214, 1610, 1498, 1479, 1260, 1033 cm-1 ; 1H NMR (CDCl3): δ7.82 (d, 2 H, J=8.9 Hz), 7.81 (d, 1 H, J=8.8 Hz), 7.28 (d, 1 H, J=2.2 Hz), 7.12 (dd, 1 H, J=8.9, 2.2 Hz), 7.02 (d, 2 H, J=8.9 Hz), 3.90 (s, 3 H), 3.88 (s, 3 H); 13C NMR (CDCl3): d 161.1, 158.5, 155.5, 131.0, 138.5, 133.1, 129.4, 124.3, 123.0, 115.8, 114.7, 104.9, 100.2, 55.8, 55.5. Anal. Calcd. for C17H13NO2S: C, 69.13; H, 4.44; N, 4.74; S, 10.85. Found: C, 68.86; H, 4.66; N, 4.52; S, 10.76.

Workup

  1. customThe cooling bath is removed
  2. customThe contents are partitioned between water and methylene chloride
  3. customthe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a solid, which
  7. customis chromatographed on silica gel (9:1 dichloromethane:toluene)

Sources & evidence

ORD record
ord-3b6929bece5d49808a22f50af5efb9bf
Source dataset
uspto-grants-2000_01
Patent number
US06018056

Reaction notes

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