Sodium Hydroxide → N-phenyl-1H-imidazol-2-amine

HRID 70053Notes

Reaction equation

HRID 70053 reaction equation
C(O[CH:4](OCC)[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[NH:8])C.[OH-].[Na+]>Cl>[C:10]1([NH:9][C:7]2[NH:8][CH:4]=[CH:5][N:6]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178467950HCID 178467950, compound

Product 1

HCID 13805404N-phenyl-1H-imidazol-2-amineYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The guanidine (b) was dissolved in HCl (5 mL, 6 M) at 0° C. and then stirred for 2 h. After the starting material was consumed, NaOH (25%) was added until a precipitate formed. This mixture was stirred for 30 min. The reaction was then poured into NaOH (0.5 M), extracted with CH2Cl2, dried and concentrated. Flash chromatography afforded (c) (0.95 g, 50%). NMR (500 MHz, DMSO-d6) δ 8.58 (s, br, 1H), 7.34-6.74 (m, 5H), 6.68 (s, 2H), 6.62 (br, 2H), 3.82 (s, 6H), 3.73 (s, 3H). MS: 157.6 (M−H)−; 160.0 (M+H)+.

Workup

  1. customAfter the starting material was consumed
  2. additionNaOH (25%) was added until a precipitate
  3. customformed
  4. stirringThis mixture was stirred for 30 min
  5. extractionextracted with CH2Cl2
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-87bf45127d404f68bb690b076455a3b7
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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