Bromine → HCID 178508261, compound

HRID 1452770Notes

Reaction equation

HRID 1452770 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([NH:13][C:14]([NH2:16])=[S:15])[NH:11][N:12]=1.BrBr>CC(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[S:15][C:14]([NH2:16])=[N:13][C:10]=2[NH:11][N:12]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178514157HCID 178514157, compound

Product 1

HCID 178508261HCID 178508261, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of [5-(2-chloro-phenyl)-2H-pyrazol-3-yl]-thiourea (2.25 g, 8.9 mmol) in glacial AcOH (900 mL) was added a 1.5 M solution of bromine in AcOH (20 mL) dropwise under vigorous stirring. The resulting heterogeneous mixture was stirred at room temperature for 2 hours then it was concentrated to dryness. Water was added followed by a saturated solution of aqueous sodium bicarbonate to neutralize to pH 7. The resulting precipitate was filtered, washed with water and dried in vacuo. Recrystallization from isopropyl alcohol afforded 1.48 g (66% yield) of 3-(2-chloro-phenyl)-1H-pyrazolo[3,4-d]thiazol-5-ylamine as a tan solid. 1H-NMR (d4-MeOH) δ: 7.64 (broad s, 1H), 7.53 (d, 1H), 7.42 (m, 2H); HPLC/MS m/z: 251 [MH]+.

Workup

  1. concentrationit was concentrated to dryness
  2. additionWater was added
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo
  6. customRecrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-a8d9751f844b414b8b81e6b148792d2d
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Reaction notes

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