Sodium Hydroxide → HCID 86597528, compound

HRID 349604Notes

Reaction equation

HRID 349604 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:8]2[CH:17]3[CH:12]([CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16]3)[NH:11][C:10](=[O:22])[C:9]=2[SH:23])[CH:7]=1.[CH2:26]([CH:28]1[O:30][CH2:29]1)Br.[OH-].[Na+]>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:8]2[CH:17]3[CH:12]([CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16]3)[NH:11][C:10](=[O:22])[C:9]=2[S:23][CH2:26][CH:28]2[CH2:29][O:30]2)[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18430Epibromohydrin2×HCID 87833560HCID 87833560, compound

Product 1

HCID 86597528HCID 86597528, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(5-Chloro-2-methoxy-phenyl)-3-oxiranylmethylsulfanyl-6-trifluoromethyl-4a,8a-dihydro-1H-quinolin-2-one (VIII) was prepared by alkylation of 4-(5-Chloro-2-methoxy-phenyl)-3-mercapto-6-trifluoromethyl-4a,8a-dihydro-1H-quinolin-2-one (Ie) with epibromohydrin. To a warm solution of Ie (2.6 mmol) and epibromohydrin (3.9 mmol) in abs. EtOH was added dropwise NaOH solution (1 Molar, 3.9 mL) forming a yellow solution. The alkylation was allowed to proceed at room temperature for an hour. The mixture was evaporated to dryness, redissolved into methylene chloride, washed with water and the organic layer dried over MgSO4. The desired product was purified by a silica-gel column eluted with mixtures of hexanes and ethyl acetate. The desired product (5) was obtained as an off-white solid in 70% yield, mp 211–212° C. Calcd. for C20H15Cl1F3N1O3S1: C, 54.34; H, 3.42; N, 3.17. Found: C, 54.35; H, 3.43, N, 3.01. 1H NMR (300 MHz, DMSO-d6) δ 7.94–7.83 (m, 2H), 7.64 (dt, J=9.0, 2.4 Hz, 1H), 7.39–7.32 (m, 3H), 5.27–5.21 (m, 1H), 4.53–4.51 (m, 1H), 3.99–3.66 (m, 4H), 3.26–3.24 (m, 1H), 3.12–3.02 (m, 1H).

Workup

  1. customforming a yellow solution
  2. waitto proceed at room temperature for an hour
  3. customThe mixture was evaporated to dryness
  4. dissolutionredissolved into methylene chloride
  5. washwashed with water
  6. dry with materialthe organic layer dried over MgSO4
  7. customThe desired product was purified by a silica-gel column
  8. washeluted with mixtures of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-c04edadb3def4548aa708ae6f21e77e1
Source dataset
uspto-grants-2007_02
Patent number
US07179920B2

Reaction notes

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