Dansyl chloride → N-Dansyl-3,5-di-(3-methylmaleimido)aniline

HRID 1470570Notes

Reaction equation

HRID 1470570 reaction equation
[S:1](Cl)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].FC(F)(F)C([O-])=O.[CH3:25][C:26]1[C:31](=[O:32])[N:30]([C:33]2[CH:34]=[C:35]([CH:37]=[C:38]([N:40]3[C:44](=[O:45])[C:43]([CH3:46])=[CH:42][C:41]3=[O:47])[CH:39]=2)[NH3+:36])[C:28](=[O:29])[CH:27]=1>N1C=CC=CC=1>[S:1]([NH:36][C:35]1[CH:37]=[C:38]([N:40]2[C:44](=[O:45])[C:43]([CH3:46])=[CH:42][C:41]2=[O:47])[CH:39]=[C:33]([N:30]2[C:31](=[O:32])[C:26]([CH3:25])=[CH:27][C:28]2=[O:29])[CH:34]=1)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 11801Dansyl chlorideHCID 680071493,5-Di-(3-methylmaleimido)anilinium trifluoroacetate

Product 1

HCID 50918100N-Dansyl-3,5-di-(3-methylmaleimido)anilineYield 16%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
25 °C

Procedure

Dansyl chloride (139 mg, 0.517 mmol) in pyridine (3 mL) was added to a pyridine solution of 4 (200 mg, 0.517 mmol). The resulting mixture was stirred at 25° C. for 18 hours after which the volatiles were evaporated under reduced pressure. The resulting oil was taken back in CHCl3 and the organic phase was washed with aqueous saturated Na2CO3, dried over MgSO4 and evaporated. The crude was purified by flash chromatography on silica gel (Tol/EtOAc 10%) giving 5 as a light green solid (40 mg, 0.074 mmol, 16%). 1H NMR (400 MHz, (CD3)2CO) δ 9.71 (s, 1H), 8.56 (d, J=8.4 Hz, 1H), 8.51 (d, J=8.8 Hz, 1H), 8.39 (dd, J1=1.2, 7.2 Hz, 1H), 7.62-7.58 (td, J=1.2, 7.2 Hz, 2H), 7.28-7.27 (m, 3H), 7.11 (t, J=2.0 Hz, 1H), 6.63-6.61 (m, 2H); 13C NMR (75 MHz, (CD3)2CO) δ 171.3, 170.4, 152.8, 135.4, 134.0, 131.7, 131.5, 130.3, 130.2, 129.6, 128.7, 124.9, 119.8, 119.6, 116.6, 115.9, 46.3, 12.1; HRMS (ESI) Calculated for C28H25N4O6S [M+H]+: 545.1516. Found: 545.1489. m.p.: 230° C.

Workup

  1. customwere evaporated under reduced pressure
  2. washthe organic phase was washed with aqueous saturated Na2CO3
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude was purified by flash chromatography on silica gel (Tol/EtOAc 10%)

Sources & evidence

ORD record
ord-b9adcad1e83e48bc8f25e2adce530a6c
Source dataset
uspto-grants-2015_04
Patent number
US09006459B2

Reaction notes

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