Iodine → HCID 57948943, compound

HRID 1992284Notes

Reaction equation

HRID 1992284 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:15][C:16]([NH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[S:17])([CH2:11][C:12]([CH3:14])=[CH2:13])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[I:27]I>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH3:10])[CH2:11][C:12]([CH2:14][I:27])([CH3:13])[S:17][C:16]([NH:18][C:19](=[O:26])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:15]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 807IodineHCID 57948923HCID 57948923, compound

Product 1

HCID 57948943HCID 57948943, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of (S)-N-(2-(3-bromo-4-fluorophenyl)-4-methylpent-4-en-2-ylcarbamothioyl)benzamide (1.3 g, 3.0 mmoles, 1.0 equiv) in dichloromethane (40 mL) is added iodine (1.5 g, 5.9 mmoles, 2.0 equiv). The reaction is stirred at 0° C. for 1 h and gradually warmed to room temperature. The reaction mixture is quenched with saturated aqueous sodium thiosulfate. The aqueous layer is extracted with dichloromethane. The combined organic phase is dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (82% yield): MS (m/z): 561, 563 (M+1).

Workup

  1. temperaturegradually warmed to room temperature
  2. customThe reaction mixture is quenched with saturated aqueous sodium thiosulfate
  3. extractionThe aqueous layer is extracted with dichloromethane
  4. dry with materialThe combined organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-22c6fa7019ad43298b4a64a8007508f0
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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