N-Iodosuccinimide → HCID 118274330, compound

HRID 522207Notes

Reaction equation

HRID 522207 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[CH:16][C:9]=23)[CH:7]=1.[I:19]N1C(=O)CCC1=O>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[C:16]([I:19])[C:9]=23)[CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 58896835HCID 58896835, compound

Product 1

HCID 118274330HCID 118274330, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Example 14A (22.4 g, 92 mmol) in acetonitrile (1 L) under nitrogen was added N-iodosuccinimide (21.84 g, 97 mmol) at ambient temperature. After stirring approximately 1 hour the reaction was complete. Solids started to crash out of the mixture and they were filtered off and washed with acetonitrile to provide the title compound as a solid. The filtrate was concentrated, mixed with 50 mL of dichloromethane, and sonicated for 30 minutes. Some solid did not dissolve and was filtered, washed with dichloromethane, and dried to give additional title compound. The filtrate was purified on an Analogix MPLC using a silica gel column eluting with 30-40% ethyl acetate/heptanes to give additional title compound. MS (ESI+) m/z 369.0 (M+H)+.

Workup

  1. filtrationwere filtered off
  2. washwashed with acetonitrile

Sources & evidence

ORD record
ord-c3269bf9935a44eb8e45c8e8fc1dae9e
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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