Methyl triflate → HCID 86600082, compound

HRID 2373133Notes

Reaction equation

HRID 2373133 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([S:57][CH2:58][C:59]3C=CC=CC=3)[CH:52]=2)[C:12]2[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]3[CH:25]=[CH:24][C:23]([N:26]([C:41]4C=CC(CCCC)=C[CH:42]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([S:33]CC5C=CC=CC=5)[CH:28]=4)=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[F:65][C:66]([F:73])([F:72])[S:67]([O:70]C)(=[O:69])=[O:68]>C(Cl)Cl.C(=O)=O.CC(C)=O>[O-:70][S:67]([C:66]([F:73])([F:72])[F:65])(=[O:69])=[O:68].[CH2:21]([C:20]1[CH:19]=[CH:18][C:41]([N:26]([C:23]2[CH:24]=[CH:25][C:20](/[CH:19]=[CH:18]/[C:15]3[CH:16]=[CH:17][C:12]([N:11]([C:8]4[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:10][CH:9]=4)[C:51]4[CH:56]=[CH:55][CH:54]=[C:53]([SH+:57][CH2:58][CH2:59][C:14]5[CH:15]=[CH:16][CH:17]=[CH:12][CH:13]=5)[CH:52]=4)=[CH:13][CH:14]=3)=[CH:21][CH:22]=2)[C:27]2[CH:28]=[C:29]([SH+:33][CH2:2][CH2:1][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:30]=[CH:31][CH:32]=2)=[CH:42][CH:25]=1)[CH2:22][CH2:23][CH3:24].[O-:70][S:67]([C:66]([F:73])([F:72])[F:65])(=[O:69])=[O:68]

Participants

5

Reactant 2

HCID 9526Methyl triflateHCID 69221590HCID 69221590, compound

Product 1

HCID 86600082HCID 86600082, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18522661Acetone cardiceSolvent

Conditions

Temperature
-78 °C

Procedure

Trans-4,4′-di[(4-n-butylphenyl)(3-benzylthiophenyl)amino]stilbene (16) (0.96 g, 1.103 mmol) was dissolved in 20 ml of dry methylene chloride and cooled at −78° C. in dry ice-acetone bath. To this solution was added, via syringe, methyl trifluoromethanesulfonate (276 μl, 2.437 mmol) and the mixture stirred for 30 min while the temperature was maintained at −78° C. The resultant mixture was then stirred two days at room temperature. After removal of some solvent under reduced pressure, the mixture was then poured into 20 ml of ether. The product was precipitated as a yellow solid, that was washed three times with ether and isolated in 80.9% (1.07 g) yield. 1H NMR (CD3COCD3, 500 MHz) δ ppm: 6.9-7.8 (m, 34 Ar—H, 2 ═CH), 5.27 (d, 2J=12.5 Hz, 2H, SCH2), 5.02 (d, 2J=12.5 Hz, 2H, SCH2), 3.53 (s, 6H, CH3), 2.63 (t, J=7.7 Hz, CH2, 4H), 1.61 (m, CH2, 4H), 1.36 (m, CH2, 4H), 0.95 (t, J=7.2 Hz, CH3, 6H)13C NMR (CD3COCD3, 125.7 MHz) δppm: 149.4, 145.6, 143.6, 139.9, 133.5, 131.8, 130.7, 130.1, 129.8, 129.3, 127.9, 127.7, 127.1, 126.5, 125.7, 124.5, 123.8, 123.4, 121.7, 51.0, 34.7, 33.5, 24.5, 22.1, 13.3. (One CF3 carbon was not observed).

Workup

  1. additionTo this solution was added, via syringe
  2. customAfter removal of some solvent under reduced pressure
  3. additionthe mixture was then poured into 20 ml of ether
  4. customThe product was precipitated as a yellow solid, that
  5. washwas washed three times with ether
  6. customisolated in 80.9% (1.07 g)
  7. customyield

Sources & evidence

ORD record
ord-f73b66c2674f492d9c707fc03ea029df
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Reaction notes

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