Pyridine → AK-660/12300001

HRID 133502Notes

Reaction equation

HRID 133502 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[C:11]([C:3]1[C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[S:6][C:2]=1[NH:1][C:25](=[O:27])[CH3:26])(=[O:12])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 6861613-Benzoyl-4,5,6,7-tetrahydro-1-benzothiophen-2-amine

Product 1

HCID 902348AK-660/12300001Yield 78%

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 1.04 g (4.04 mmol) (2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-phenyl-methanone in 25 ml acetic anhydride was added 0.2 ml pyridine. The mixture was heated at 50° C. for 35 minutes and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford 1.35 g (78%) N-(3-benzoyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-acetamide as an orange oil. ES-MS m/e (%): 300 (M+H+, 100).

Workup

  1. additionpoured onto water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3692dfbc9a84dd59ba1c70f08257f22
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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