Hydrazine hydrate (1:1) → HCID 178433091, compound

HRID 560850Notes

Reaction equation

HRID 560850 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[S:11][C:10]([N:12]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[C:13]2=[O:28])=[N:9][C:8]=1[CH3:29])=O.O.[NH2:32]N>C(O)C>[CH3:29][C:8]1[N:9]=[C:10]([N:12]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:23]=3)[C:13]2=[O:28])[S:11][C:7]=1[C:5]1[CH:4]=[CH:3][NH:2][N:32]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58031425HCID 58031425, compound

Product 1

HCID 178433091HCID 178433091, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (E)-1-(5-(3-(dimethylamino)acryloyl)-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)imidazolidin-2-one (0.44 g, 1.00 mmol) in ethanol (10 mL) was added hydrazine monohydrate (0.12 mL, 1.58 mmol). The reaction mixture was heated to reflux for 3 hours. The solvent was removed in vacuo, and the residue was purified by column chromatography to afford the title compound as a colorless solid in 72% yield (0.30 g): mp 212-213° C. (ethyl acetate): 1H NMR (300 MHz, CDCl3& CD3OD) δ 7.54-7.20 (m, 5H), 6.24 (s, 1H), 4.39 (s, 2H), 3.98-3.89 (m, 2H), 3.35-3.30 (m, 2H), 2.27 (s, 3H): 13C NMR (75 MHz, CDCl3 & CD3OD) δ 156.9, 155.8, 139.8, 130.2, 129.8, 129.3, 128.2, 125.6, 125.5, 122.0, 103.8, 47.2, 41.9, 41.8, 15.7: MS (ES+) m/z 408.1 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2ff3be03c76f4e30b4e1b1d5671057bf
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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