1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68328141, compound

HRID 634335Notes

Reaction equation

HRID 634335 reaction equation
[CH:1]([NH:4][C:5]([NH:7][NH:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[N+:20]([O-:22])=[O:21])=[O:10])=S)([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl>C1(C)C=CC=CC=1>[CH:1]([NH:4][C:5]1[O:10][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[N+:20]([O-:22])=[O:21])=[N:8][N:7]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86725121HCID 86725121, compound

Product 1

HCID 68328141HCID 68328141, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of N-isopropyl-2-(3-nitro-1H-indole-5-carbonyl)hydrazinecarbothioamide (1.5 g, 4.672 mmol) in toluene (15 mL) was added EDC HCl (1.3 g, 7.009 mmol) in one lot and the reaction was heated to reflux for 16 h. After completion, toluene was removed in vacuo and the residue was treated with water (25 mL) to get a precipitate. The precipitate was filtered washed and dried. The crude product was washed with 10% EtOAc in petroleum ether to afford N-isopropyl-5-(3-nitro-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (1.2 g, 92%) as pale yellow colored solid. MS (ESI, pos. ion) m/z: 288.1 (M+1); 1H-NMR (300 MHz, DMSO-d6): δ 12.88 (brs, 1H), 8.75 (s, 1H), 8.47 (s, 1H), 7.67-7.84 (m, 3H), 3.69-3.76 (m, 1H), 1.21 (d, 6H, J=6.6 Hz).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 16 h
  3. customAfter completion, toluene was removed in vacuo
  4. additionthe residue was treated with water (25 mL)
  5. customto get a precipitate
  6. filtrationThe precipitate was filtered
  7. washwashed
  8. customdried
  9. washThe crude product was washed with 10% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-76584e6d61dc4d14931ac29a93b3a899
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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