Water → HCID 178477994, compound

HRID 41879Notes

Reaction equation

HRID 41879 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:20]=[CH:19][NH:18][N:17]=2)=[CH:12][CH:11]=1.O>C(Cl)Cl>[Br:1][C:20]1[C:16]([C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][CH:14]=2)=[N:17][NH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 178477945HCID 178477945, compound

Product 1

HCID 178477994HCID 178477994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Bromosuccinimide (10.4 g, 56.0 mmol) was added portionwise to a solution of 3-(4-chlorophenyl)-1H-pyrazole (10.0 g, 56.0 mmol) in CH2Cl2 (140 mL). The mixture was stirred for 10 min, water and an additional portion of CH2Cl2 were added and the mixture was stirred for 5 min. The organic phase was separated, washed with brine, dried (MgSO4) and concentrated to yield 15.0 g of Ex 3-Step 1 product as a light yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.68 (d, J=8.6, 2H), 7.59 (s, 1H), 7.35-7.39 (m, 2H).

Workup

  1. stirringthe mixture was stirred for 5 min
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto yield 15.0 g of Ex 3-Step 1 product as a light yellow solid

Sources & evidence

ORD record
ord-6f6a91b321204d70bedd4be8527395a2
Source dataset
uspto-grants-2013_09
Patent number
US08536164B2

Reaction notes

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