Methyl p-toluenesulfonate → HCID 86671700, compound

HRID 2191171Notes

Reaction equation

HRID 2191171 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][N:6]1[CH:14]([OH:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]1[OH:16])[CH3:2].[CH3:19][O:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>C1(C)C=CC=CC=1>[C:27]1([CH3:30])[CH:26]=[CH:25][C:24]([S:21]([O-:23])(=[O:20])=[O:22])=[CH:29][CH:28]=1.[O:16]=[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14](=[O:15])[N:6]1[CH2:5][CH2:4][N+:3]([CH2:1][CH3:2])([CH2:17][CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 68379267HCID 68379267, compound

Product 1

HCID 86671700HCID 86671700, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.0 g (81.3 mmol) of 2-[2-(diethylamino)ethyl]-1H-isoindole-1,3(2H)-diol from stage 1 and 16.6 g (89.5 mmol) of p-toluenesulfonic acid methyl ester were refluxed in 250 ml toluene for 8 hours. After cooling, the white, crystalline solid was filtered out and rewashed with toluene. The product was then dried under a vacuum at 30° C. Yield: 10.3 g (29.3%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=1.39 (t, 6H); 2.28 (s, 3H); 3.06 (s, 3H); 3.47 (m, 6H); 3.97 (q, 2H); 7.10 (d, 2H); 7.48 (d, 2H); 7.89 (m, 4H); 13C-NMR (400 MHz, DMSO-d6): δ [ppm]=8.1; 20.7; 30.5; 46.1; 55.5; 56.0; 123.2; 125.4; 128.0; 131.2; 134.5; 137.6; 145.6; 167.3.

Workup

  1. temperatureAfter cooling
  2. filtrationthe white, crystalline solid was filtered out
  3. customThe product was then dried under a vacuum at 30° C

Sources & evidence

ORD record
ord-ae13a5d423294cc28c904198bb2bba87
Source dataset
uspto-grants-2012_12
Patent number
US08328879B2

Reaction notes

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