Aniline → HCID 72639908, compound

HRID 1241941Notes

Reaction equation

HRID 1241941 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:12]([N:19]1[C:23](=[O:24])[C:22](=[C:25]2[N:29]([CH3:30])[C:28]3[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=3[S:26]2)[S:21][CH2+:20]1SC)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CC#N>[CH2:12]([N:19]1[C:23](=[O:24])[C:22](=[C:25]2[N:29]([CH3:30])[C:28]3[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=3[S:26]2)[S:21][C:20]1=[N:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 6115Aniline

Product 1

HCID 72639908HCID 72639908, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To an 8 mL vial was added 3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-methylthio-4-oxo-2-thiazolium p-toluenesulfonate (100 mg, 0.18 mmol), aniline (16 μL, 0.18 mmol) and anhydrous MeCN (1 mL). After warming the mixture to 50° C., TEA (0.10 mL, 0.56 mmol) was added and continued heating the mixture at 50° C. for 12 h. After cooling to room temperature, the resulting precipitates were filtered under reduced pressure, washed with MeCN (2 mL) and dried under vacuum to yield the title product (22.3 mg, 29%) as a yellow solid. 1H-NMR (CDCl3): δ 7.59 (2H, m), 7.48 (1H, dd), 7.26–7.39 (6H, m), 7.10–7.18 (2H, m) 7.01 (3H, m), 5.16 (2H, s), 3.71 (3H, s); MS(ESI): 430 (MH+).

Workup

  1. temperaturecontinued heating the mixture at 50° C. for 12 h
  2. temperatureAfter cooling to room temperature
  3. customthe resulting precipitates
  4. filtrationwere filtered under reduced pressure
  5. washwashed with MeCN (2 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-1a7017b299064d869dfbd6b55e9e6d70
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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