Potassium Iodide → HCID 23435736, compound

HRID 2120963Notes

Reaction equation

HRID 2120963 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]2[CH2:20][CH2:19][C:12]3([NH:16][C:15](=[O:17])[NH:14][C:13]3=[O:18])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1)#[N:2].Cl[CH2:24][CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[CH2:20][CH2:19][C:12]3([NH:16][C:15](=[O:17])[N:14]([CH2:24][CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:13]3=[O:18])[CH2:11][CH2:10]2)=[O:8])=[CH:21][CH:22]=1)#[N:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 527695Butanoic acid, 4-chloro-, 1,1-dimethylethyl esterHCID 23435772HCID 23435772, compound

Product 1

HCID 23435736HCID 23435736, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.4 g (8.0 mmol) of the compound from Step B, 1.8 g (10.1 mmol) tert.-butyl 4-chlorobutanoate (prepared according to Chem. Ber. 1965, 98, 2312), 2.8 g (20.3 mmol) dry potassium carbonate, and a catalytic amount potassium iodide in 50 ml dry DMF was heated at 100° C. for 6 h until the conversion was complete. It was poured into ice-cold water, and the crude solid title compound was collected by filtration. It was redissolved in hot ethyl acetate and dried over sodium sulfate, which was removed by filtration. The title hydantoin crystallized from the filtrate by addition of hexane.

Workup

  1. additionIt was poured into ice-cold water
  2. filtrationthe crude solid title compound was collected by filtration
  3. dissolutionIt was redissolved in hot ethyl acetate
  4. dry with materialdried over sodium sulfate, which
  5. customwas removed by filtration
  6. customThe title hydantoin crystallized from the filtrate by addition of hexane

Sources & evidence

ORD record
ord-6ed19d024e204bd29c26cd17b907e926
Source dataset
uspto-grants-2004_02
Patent number
US06693109B2

Reaction notes

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