Diisopropylethylamine → 1-{[5-Bromo-4-(3-chlorophenyl)furan-2-yl]carbonyl}imidazolidin-4-one

HRID 2190131Notes

Reaction equation

HRID 2190131 reaction equation
BrC1C=C(C([N:16]2C[CH2:20][NH:19][C:18](=[O:22])[CH2:17]2)=O)OC=1C1C=CC=C(Cl)C=1.[Br:23][C:24]1[O:28][C:27]([C:29]([OH:31])=O)=[CH:26][C:25]=1[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=1.C(N(CC)C(C)C)(C)C>>[Br:23][C:24]1[O:28][C:27]([C:29]([N:16]2[CH2:17][C:18](=[O:22])[NH:19][CH2:20]2)=[O:31])=[CH:26][C:25]=1[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 580647644-{[4-Bromo-5-(3-chlorophenyl)furan-2-yl]carbonyl}piperazin-2-oneHCID 580648025-Bromo-4-(3-chlorophenyl)furan-2-carboxylic acid

Product 1

HCID 580647691-{[5-Bromo-4-(3-chlorophenyl)furan-2-yl]carbonyl}imidazolidin-4-one

Procedure

The preparation of the title compound takes place in analogy to the synthesis of the compound from Example 27A starting with the compound from Example 22A and the compound from Example 35A. 3.5 equivalents of N,N-diisopropylethylamine are used. During the reaction, the product precipitates. The precipitate is collected by suction filtration, washed with tetrahydrofuran and dried under high vacuum. 1.17 g (100% of theory) of the title compound are obtained.

Workup

  1. customDuring the reaction
  2. customthe product precipitates
  3. filtrationThe precipitate is collected by suction filtration
  4. washwashed with tetrahydrofuran
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-704eba238ef14d22a5700948cafe02a1
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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