Water → HCID 178424864, compound

HRID 2088714Notes

Reaction equation

HRID 2088714 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:9](OC)=[O:10])[C:3]1=O.[N+]([O-])(O)=O.[NH2:19][C:20]([NH2:22])=[NH:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.CC(O)=O>[NH2:22][C:20]1[N:19]=[C:9]([OH:10])[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:2]([CH3:14])([CH3:1])[C:3]=2[N:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10481Guanidine NitrateHCID 11430Potassium CarbonateHCID 68923799HCID 68923799, compound

Product 1

HCID 178424864HCID 178424864, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 1B (1.668 g, 8.41 mmol), guanidine nitrate (2.054 g, 16.83 mmol), and potassium carbonate (2.326 g, 16.83 mmol) was heated in DMF (17 mL) at 120° C. overnight. After this time, the mixture was cooled to room temperature and poured into water. The liquid was adjusted to pH 5 with HOAc, then the precipitate was collected by filtration, washed with water, and air-dried. It was further dried by azeotroping with toluene to yield the title compound. 1H NMR (300 MHz, DMSO-d6) δ 10.59 (br, 1H), 6.02 (br, 2H), 2.57 (m, 2H), 1.48-1.71 (m, 6H), 1.19 (s, 6H). MS (DCI+) m/z 208 (M+H)+.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. customair-dried
  4. customIt was further dried
  5. customby azeotroping with toluene

Sources & evidence

ORD record
ord-9d09e17c524943ee9934847e2fb42c26
Source dataset
uspto-grants-2013_05
Patent number
US08436005B2

Reaction notes

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