1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → HCID 89851886, compound

HRID 1771450Notes

Reaction equation

HRID 1771450 reaction equation
[CH3:1][CH:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:9]3[C:10]=2[C:5](=[CH:6][CH:7]=[CH:8]3)[CH:4]([C:15]#[N:16])[O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:28](N)[CH2:29][NH2:30]>>[CH3:1][CH:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:9]3[C:10]=2[C:5](=[CH:6][CH:7]=[CH:8]3)[CH:4]([C:15]2[NH:30][CH2:29][CH2:28][N:16]=2)[O:3]1

Participants

3

Reactant 2

HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 117925624HCID 117925624, compound

Product 1

HCID 89851886HCID 89851886, compoundYield 9.1%

Conditions

Temperature
200 °C

Procedure

3-Methyl-1,3-dihydrobenzo[de]isochromene-1-carbonitrile (100 mg) was mixed with ethylene diamine mono-p-toluenesulfonic acid salt (111 mg) and the mixture was heated to 200° C. After 3 hours reaction was cooled to room temperature. Purification of the mixture by column chromatography with neutral alumina (ethyl acetate-heptane) afforded 11 mg of 2-(3-methyl-1,3-dihydrobenzo[de]isochromen-1-yl)-4,5-dihydro-1H-imidazole that was converted to the title compound using salt formation method A. (Yield 10 mg).

Workup

  1. customAfter 3 hours reaction
  2. temperaturewas cooled to room temperature
  3. customPurification of the mixture by column chromatography with neutral alumina (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-1722c8e8d68e486b936ec5c658dfdf04
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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