HCID 10847260, compound → HCID 10632465, compound

HRID 1737297Notes

Reaction equation

HRID 1737297 reaction equation
[CH2:1]([C:9]1([NH:15][CH:16]=O)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(Cl)Cl.CC(O)C>[O:12]1[CH2:13][CH2:14][C:9]2([N:15]=[CH:16][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH2:2][CH2:1]2)[CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 10847260HCID 10847260, compound

Product 1

HCID 10632465HCID 10632465, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 21966342Isopropanol methylene chlorideSolvent

Procedure

Formamide 20 (3.65 g, 15.7 mmol) from the previous experiment is cyclized according to general procedure C to give imine 22 (0.47 g, 14%) as a yellow oil after FC (10:1 CH2Cl2 /iPrOH). 1H NMR (CDCl3) 8.35(s,1) , 7.50-7.45(m,1) 7.40-7.20(m,3), 4.10-3.95(m,2), 3.85-3.70(m,2), 3.15-3.05(m,2), 2.00-1.95(m,2), 1.85-1.70(m,4); 13C NMR (CDCl3) 157.88, 141.77, 135.23, 132.61, 129.89, 129.66, 126.21, 64.02, 58.32, 38.71, 37.25, 30.13; MS(MW=215.3, CI/CH4, eE=120 eV) m/z 216 [(M+H+), base peak], 199, 189, 171, 143, 117, 100, 83.

Sources & evidence

ORD record
ord-b47da9bf493c441497b444b231fc8cc7
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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