Hydrogen Bromide → HCID 178434639, compound

HRID 407356Notes

Reaction equation

HRID 407356 reaction equation
OS(O)(=O)=O.[BrH:6].[NH2:7][C:8]1[NH:12][N:11]=[C:10]([CH3:13])[C:9]=1[C:14]1[S:15][C:16]2[CH:22]=[C:21]([CH2:23]O)[CH:20]=[CH:19][C:17]=2[N:18]=1.[OH-].[Na+]>>[Br:6][CH2:23][C:21]1[CH:20]=[CH:19][C:17]2[N:18]=[C:14]([C:9]3[C:10]([CH3:13])=[N:11][NH:12][C:8]=3[NH2:7])[S:15][C:16]=2[CH:22]=1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 178434645HCID 178434645, compound

Product 1

HCID 178434639HCID 178434639, compound

Procedure

To a solution of concentrated H2SO4 (0.3 mL) and hydrobromic acid (0.6 mL, 48%) was added [2-(5-amino-3-methyl-1H-pyrazol-4-yl)-benzothiazol-6-yl]-methanol (52 mg, 0.2 mmol). The resulting mixture was refluxed for 2 hrs. Upon cooling to room temperature, the mixture was poured into ice water resulting a milky solution. The suspension was neutralized to pH 3-4 with 5% NaOH solution. The resulting cream coloured solid was isolated by filtration, washed with water and air-dried to yield 58 mg of 4-(6-bromomethylbenzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine. The crude material was used in the subsequent step without further purification.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hrs
  2. customwas isolated by filtration
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-389ab55260b54185bea1efd97631a2c8
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

Loading…