2-Methyl-1,3-propanediamine → HCID 178457537, compound

HRID 47159Notes

Reaction equation

HRID 47159 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][CH:19]([CH3:22])[CH2:20][NH2:21]>C(#N)C>[NH2:17][CH2:18][CH:19]([CH3:22])[CH2:20][NH:21][C:2]([CH3:16])([CH3:15])[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 2

HCID 144990522-Methyl-1,3-propanediamineHCID 178448405HCID 178448405, compound

Product 1

HCID 178457537HCID 178457537, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ0.89(d, 3H, CH3), 1.22[s, 6H, C(CH3)2], 1.51(m, 1H, CH3CH), 2.25(d, 2H, CH2NH2), 2.65(m, 2H, NHCH2), 5.31(s, 2H, imi-CH2), 7.03 & 7.21(2s, 2H, imi-H). MS m/e 299 (M+H)+.

Workup

  1. additionAfter the addition the reaction mixture
  2. temperatureThe reaction mixture was then cooled
  3. customsolvent was removed on a rotary evaporator to
  4. customa give a paste
  5. customThis was crystallized from dichloromethane-ether

Sources & evidence

ORD record
ord-b143c0d29a784d1c9ae4c2dde5db77b5
Source dataset
uspto-grants-2004_03
Patent number
US06699458B2

Reaction notes

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