Hydrochloric Acid → HCID 178424372, compound

HRID 1441173Notes

Reaction equation

HRID 1441173 reaction equation
Cl.Cl.[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=1[CH3:21])=[NH:12].Cl.N([O-])=O.[Na+].[N-:27]=[N+:28]=[N-].[Na+].N#N.[OH-].[Na+]>O>[CH3:21][C:15]1[CH:16]=[C:17]([N:20]=[N+:27]=[N-:28])[CH:18]=[CH:19][C:14]=1[NH:13][C:11]([NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH3:3])=[NH:12]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 178424371HCID 178424371, compound

Product 1

HCID 178424372HCID 178424372, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

N-(2-Methylphenyl)-N'-(2-methyl-4-aminophenyl)guanidine dihydrochloride (112 mg, 0.341 mmol) were dissolved in 2 ml H2O and 100 ul conc. HCl (1.2 mmol). The solution was cooled in an ice bath, and a solution of NaNO2 (42 mg, 0.61 mmol) in 450 ul H2O were added. The reaction mixture turned yellow, and was stirred for 45 min before solid NaN3 (43 mg, 0.661 mmol) was added in a single portion. After N2 evolution was caused, a foamy solid (11 mg) was removed and discarded. Solid NaOH (96 mg, 2.41 mmol) was added, and the bright yellow precipitate was extracted with Et2O (3×5 ml). Evaporation of the combined Et2O layers gave a yellow solid which was crystallized from EtOH/H2O: NMR (CD3OD) 2.279 (s, 3 H), 2.284 (s, 3 H), 6.864 (dd, 1H, J=2.4 Hz, 8.4 Hz), 6.914 (d, 1H, J=2.1 Hz), 7.055 (td, 1H, J=1.8 Hz, 7.2 Hz), 7.136-7.229 (m, 4H).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. additionwas added in a single portion
  3. customa foamy solid (11 mg) was removed
  4. extractionthe bright yellow precipitate was extracted with Et2O (3×5 ml)
  5. customEvaporation of the combined Et2O layers
  6. customgave a yellow solid which
  7. customwas crystallized from EtOH/H2O

Sources & evidence

ORD record
ord-c0ce33d1e89e471ea4af2f875b3d1a8f
Source dataset
uspto-grants-1996_03
Patent number
US05502255

Reaction notes

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