Methyl p-toluenesulfonate → HCID 86593320, compound

HRID 2224001Notes

Reaction equation

HRID 2224001 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[S:12][C:13]4[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=4[N:15]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[S:20]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([O:23][CH3:24])(=[O:22])=[O:21]>>[S:20]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([O-:23])(=[O:22])=[O:21].[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[S:12][C:13]4[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=4[N:15]=3)[CH:8]=[CH:7][C:5]=2[N+:6]=1[CH3:24]

Participants

3

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 179535072'-Methyl-2,6'-bi-1,3-benzothiazole

Product 1

HCID 86593320HCID 86593320, compound

Procedure

2-methyl-6-(benzothiazol-2-yl)-benzothiazole (44 mg, 0.156 mmol) was stirred for 5 h at 90° C. in melted methyl tosylate (660 mg, 3.5 mmol). After being allowed to cool to room temperature, the product was precipitated by addition of acetone and collected by filtration. The precipitate was washed with acetone and allowed to dry over night. This gave the product as green crystals. Yield: 51 mg, 70%. 1H NMR (DMSO): δ 2.28 (s, 3H, —CH3), 3.20 (s, 3H, CH3), 4.24 (s, 3H, —CH3), 7.11 (d, J=7.2, 2H, ArH), 7.46 (d, J=7.2, 2H, ArH), 7.55 (t, J=7.6, 1H, ArH), 7.62 (t, J=7.6, 1H, ArH), 8.14 (d, J=8, 1H, ArH), 8.25 (d, J=8, 1H, ArH), 8.45 (d, J=8.8, 1H, ArH), 8.59 (d, J=8.8, 1H, ArH), 9.24 (s, 1H, ArH). HR-FAB-MS m/z Found: 297.067 C16H13N2S2 (M+): requires M, 297.052.

Workup

  1. customthe product was precipitated by addition of acetone
  2. filtrationcollected by filtration
  3. washThe precipitate was washed with acetone
  4. customto dry over night

Sources & evidence

ORD record
ord-7223b56b68724768b1145f534a6b8a8f
Source dataset
uspto-grants-2008_05
Patent number
US07378240B2

Reaction notes

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