2,3-Dimethylaniline → HCID 178425510, compound

HRID 1886438Notes

Reaction equation

HRID 1886438 reaction equation
CC1C(C)=CC=CC=1N.N1CCN=C1S(O)(=O)=O.[C:19]1([N:29]=[C:30]2[NH:34][CH2:33][CH2:32][NH:31]2)[C:28]2[CH2:27]CC[CH2:24][C:23]=2[CH:22]=[CH:21][CH:20]=1>CC#N>[CH3:27][C:28]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=1[N:29]=[C:30]1[NH:31][CH2:32][CH2:33][NH:34]1

Participants

5

Reactant 3

HCID 68932,3-DimethylanilineHCID 2745614,5-dihydro-1H-imidazole-2-sulfonic acid2×HCID 178419826HCID 178419826, compound

Product 1

HCID 178425510HCID 178425510, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
155 °C

Procedure

2,3 Dimethylaniline (Aldrich, 236 mg, 1.95 mmol), imidazoline-2-sulfonic acid (292 mg, 1.95 mmol, (Compound 7 obtained as described above)) and CH3CN (4 ml) were placed in a thick-walled glass tube and sealed with a TEFLON™ screw-cap. The reactants were heated to 155° C. for 6 hours. The reaction was worked up as described for Compound 4 and chromatographed (SiO2 ; 70:30 CHCl3 /CH3OH saturated with NH3) to yield a light yellow oil which was recrystallized (hexane/isopropanol to yield 61 mg (17%) of the title compound as an off-white crystalline solid: mp 141°-144° C.; 1H NMR (300 MHz, CDCl3) & 6.98 (m, 1H); 6.80 (m, 2H), 5.31 (br, 2H); 3.42 (s, 4H); 2.31 (s, 3H); 2.12 (s, 3H); Mass spectrum m/e 189.1259 (C11H 15 N3 requires 189.1266). Alternatively, and preferably alcohols, most preferably isobutanol, are used instead of CH3CN in this reaction.

Workup

  1. customscrew-cap
  2. customchromatographed (SiO2 ; 70:30 CHCl3 /CH3OH saturated with NH3)
  3. customto yield a light yellow oil which
  4. customwas recrystallized (hexane/isopropanol

Sources & evidence

ORD record
ord-52eb238492be491aad5eca19353e513f
Source dataset
uspto-grants-1992_09
Patent number
US05151440

Reaction notes

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