N-bromobutanimide → HCID 20324950, compound

HRID 838854Notes

Reaction equation

HRID 838854 reaction equation
[CH2:1]([C:6]1[N:11]2[N:12]=[CH:13][CH:14]=[C:10]2[N:9]=[C:8]([C:15]([F:18])([F:17])[F:16])[CH:7]=1)[CH2:2][CH:3]([CH3:5])[CH3:4].[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:19][C:14]1[CH:13]=[N:12][N:11]2[C:6]([CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])=[CH:7][C:8]([C:15]([F:16])([F:17])[F:18])=[N:9][C:10]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20324949HCID 20324949, compound

Product 1

HCID 20324950HCID 20324950, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4.0 gm (0.0155 mol) of 7-isopentyl-5-trifluoromethylpyrazolo[1,5-a]pyrimidine in 50 ml chloroform was cooled to 15° and 2.73 gm. (0.0155 mol) of N-bromosuccinimide was added. The solution was stirred for 30 minutes at ambient temperature, then poured on ice (50 gm, crushed). The chloroform layer was washed with sat. K2CO3 solution and then dried (Na2SO4) and chromatographed on neutral alumina (Woelm, grade I). Elution of the compound with chloroform, followed by evaporation of the solvent and distillation, afforded 4.0 gm (58%) of the product as an amber oil, b.p. 123°-126° /0.5 mm.

Workup

  1. additionpoured on ice (50 gm, crushed)
  2. washThe chloroform layer was washed with sat. K2CO3 solution
  3. dry with materialdried (Na2SO4)
  4. customchromatographed on neutral alumina (Woelm, grade I)
  5. washElution of the compound with chloroform
  6. customfollowed by evaporation of the solvent and distillation

Sources & evidence

ORD record
ord-49779c2d827d44e492362a7089fd221d
Source dataset
uspto-grants-1978_06
Patent number
US04093617

Reaction notes

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