Water → HCID 67435580, compound

HRID 1496629Notes

Reaction equation

HRID 1496629 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:15]=1)[CH3:10].O>ClCCl>[Br:1][C:13]1[S:12][C:11]([CH2:9][CH3:10])=[N:15][C:14]=1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 57471692HCID 57471692, compound

Product 1

HCID 67435580HCID 67435580, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 1.72 g (9.64 mmol) of N-bromosuccinimide are added a little at a time to a solution of 2.00 g (9.64 mmol) of 2-ethyl-4-(4-fluorophenyl)-1,3-thiazole in 40 ml of dichloromethane. After 2 h, 50 ml of water are added to the reaction mixture, and the organic phase is separated off, washed with saturated NHCO3 solution, dried over MgSO4 and concentrated under reduced pressure. This gives 2.47 g (85%) of the desired product; 1H-NMR(DMSO-d6) δ: 7.92 (m, 2H), 7.32 (m, 2H), 3.02 (q, 2H), 1.31 (t, 3H).

Workup

  1. customthe organic phase is separated off
  2. washwashed with saturated NHCO3 solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d76d40b15ec047a1847095d36fc3b594
Source dataset
uspto-grants-2015_12
Patent number
US09198426B2

Reaction notes

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