Ethylenediamine → HCID 59736829, compound

HRID 252835Notes

Reaction equation

HRID 252835 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][C:3]=1[NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1.[CH2:24](N)[CH2:25][NH2:26].C(=S)=S>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][C:3]=1[NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[NH:26][CH2:25][CH2:24][N:22]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6348Carbon DisulfideHCID 59736923HCID 59736923, compound

Product 1

HCID 59736829HCID 59736829, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-Amino-5-(thiophen-2-yl)phenyl)-4-cyanobenzamide 173 (30 mg, 0.1 mmol), ethylenediamine (0.126 mL, 1.9 mmol.) and carbon disulfide (catalyst) were stirred at 50° C. in DMF overnight. The reaction mixture was then evaporated to dryness, taken up in methanol and filtered to give the title compound 174 as a yellow solid (16.3 mg, 48%). 1H NMR: (DMSO) δ (ppm): 400 MHz, (DMSO) d (ppm): 9.78 (s, 1H), 8.02 (d, J=8.0 Hz, 2H), 7.92 (d, J=8.0 Hz, 2H), 7.45 (s, 1H), 7.33 (d, J=5.1 Hz, 1H), 7.28 (d, J=8.2 Hz, 1H), 7.22 (d, J=3.3 Hz, 1H), 7.03 (t, J=3.9 Hz, 1H), 6.79 (d, J=8.2 Hz, 1H), 5.18 (s, 2H), 3.63 (s, 4H). MS: 362.12 (calc), 363.1 (obs).

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a9e7ee882d78494b999a4bf09d8ca50a
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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