1,3-Propanediamine → HCID 178444777, compound

HRID 47162Notes

Reaction equation

HRID 47162 reaction equation
Cl[C:2]([CH3:16])([CH3:15])[CH:3]([N:13]=[O:14])[CH2:4][C:5]1[N:6]=[C:7]([N+:10]([O-:12])=[O:11])[NH:8][CH:9]=1.[NH2:17][CH2:18][CH2:19]CN.[C:22](#N)C>>[NH2:17][CH2:18][CH2:19][CH2:15][C:2]([CH3:16])([CH3:22])[C:3](=[N:13][OH:14])[CH2:4][C:5]1[N:6]=[C:7]([N+:10]([O-:12])=[O:11])[NH:8][CH:9]=1

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 6342AcetonitrileHCID 178448405HCID 178448405, compound

Product 1

HCID 178444777HCID 178444777, compound

Conditions

Temperature
50 °C

Procedure

3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.00 g, 4.06 mmol,Example 1) was added in portions over a period of 20 minutes to a stirred solution of 1,3-diaminopropane (1.0 g, 13.50 mmol) in dry acetonitrile at 50° C. After the addition, the reaction mixture was maintained at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and filtered to provide the title compound as a yellow colored solid. For further purification, the solid was suspended in a small amount of water, stirred and filtered to afford the title product in >97% purity; yield: 0.78 g, (68%); mp. 136-137° C. 1H NMR (DMSO-d6) δ1.19[s, 6H, C(CH3)3], 1.37(m, CH2CH2CH2), 1.52(bs, 1N, NH), 2.21 & 1.54(2t, 4H, NHCH2), 5.22(s, 2H, imida-CH2), 7.05 & 7.27(2s, 2H, imida-ring H) and 11.42(bs, 1H, NOH). MS m/e 285 (M+H)+.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f0ddd857be49408591696b92ff5c4e02
Source dataset
uspto-grants-2004_03
Patent number
US06699458B2

Reaction notes

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