Hydrochloric Acid → HCID 86614746, compound

HRID 2108285Notes

Reaction equation

HRID 2108285 reaction equation
Cl.[NH2:2][C:3]1[S:4][C:5]([CH3:9])=[C:6]([CH3:8])[N:7]=1.[N:10](OS(=O)(=O)O)=O.[Br-:17].[CH2:18]([N:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:21][CH2:22][N+:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19].Cl.[OH-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O>[Br-:17].[CH3:8][C:6]1[N:7]=[C:3]([N:2]=[N:10][C:30]2[CH:29]=[CH:28][C:27]([N:20]([CH2:18][CH3:19])[CH2:21][CH2:22][N+:23]([CH3:26])([CH3:24])[CH3:25])=[CH:32][CH:31]=2)[S:4][C:5]=1[CH3:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 82157Nitrosylsulfuric acidHCID 162113874,5-Dimethyl-1,3-thiazol-2-amine--hydrogen chloride (1/1)HCID 68540811HCID 68540811, compound

Product 1

HCID 86614746HCID 86614746, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
15 °C

Procedure

11.5 g 2-amino-4,5-dimethyl-1,3-thiazol hydrochloride is dissolved in a mixture of 300 ml acetic acid and 10.2 g sulphuric acid while the temperature rises up to 30° C. The mixture is cooled to 15° C. followed by dropwise addition of 33.2 g 40% aqueous nitrosyl sulphuric acid and is stirred for 1.5 hours. In a separate beaker a solution of 20 g 2-[ethyl(phenyl)amino]-N,N,N-trimethylethanaminium bromide in a mixture of 80 ml acetic acid, 8.3 g hydrochloric acid and 120 g ice was prepared. The previously prepared diazonium salt solution was added slowly to this solution so that the temperature does not exceed 5° C. The solution is further stirred for 2 hours at room temperature. The pH value is adjusted to 4 by adding an appropriate amount of 30% aqueous sodium hydroxide. The resulted precipitate is filtered off, washed with water, and dried in vacuum at 40° C. After recrystallization in ethanol/water, 20.3 g of 2-[{4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]phenyl}(ethyl)amino]-N,N,N-trimethylethanaminium bromide is obtained as red crystals.

Workup

  1. customrises up to 30° C
  2. customwas prepared
  3. customdoes not exceed 5° C
  4. stirringThe solution is further stirred for 2 hours at room temperature
  5. filtrationThe resulted precipitate is filtered off
  6. washwashed with water
  7. customdried in vacuum at 40° C
  8. customAfter recrystallization in ethanol/water

Sources & evidence

ORD record
ord-8e49e68ee0634816aedf3e3f72e318a4
Source dataset
uspto-grants-2009_04
Patent number
US07513917B2

Reaction notes

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