Water → 2-[4-Bromo-5-(4-fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]benzothiazole

HRID 1032454Notes

Reaction equation

HRID 1032454 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]([C:21]3[S:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[N:25]=3)[N:19]=[C:18]([CH:30]([CH3:32])[CH3:31])[CH:17]=2)=[CH:12][CH:11]=1.O>CN(C=O)C>[Br:1][C:17]1[C:18]([CH:30]([CH3:32])[CH3:31])=[N:19][N:20]([C:21]2[S:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)[C:16]=1[C:13]1[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 148513332-[5-(4-Fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]benzothiazole

Product 1

HCID 148513342-[4-Bromo-5-(4-fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]benzothiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Bromosuccinimide (86.5 g, 486 mmol) was added in portions to the pyrazole (164 g, 486 mmol, Step A) in DMF (1l) at 0° C. under an atmosphere of N2. This mixture was stirred and allowed to warm to room temperature overnight. The reaction mixture was poured into H2O (1 l) and the resulting precipitate was collected and washed with water. The product was dried overnight to give 184.1 g (91%), mp 146°-147° C. (hexanes).

Workup

  1. customthe resulting precipitate was collected
  2. washwashed with water
  3. customThe product was dried overnight
  4. customto give 184.1 g (91%), mp 146°-147° C. (hexanes)

Sources & evidence

ORD record
ord-3f3ddc96d445454aafff1af970d22a69
Source dataset
uspto-grants-1990_09
Patent number
US04957971

Reaction notes

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