Pyridine → 3-n-Butyl-5-(4-cyanobenzyl) hydantoin

HRID 847726Notes

Reaction equation

HRID 847726 reaction equation
FC(F)(F)C([NH:5]OC(=O)C(F)(F)F)=O.N1C=CC=CC=1.[CH2:21]([N:25]1[C:29](=[O:30])[CH:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([CH:38]=O)=[CH:34][CH:33]=2)[NH:27][C:26]1=[O:40])[CH2:22][CH2:23][CH3:24]>C1C=CC=CC=1>[CH2:21]([N:25]1[C:29](=[O:30])[CH:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]#[N:5])=[CH:34][CH:33]=2)[NH:27][C:26]1=[O:40])[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 69634(2,2,2-Trifluoroacetyl)azanyl 2,2,2-trifluoroacetateHCID 127907213-n-Butyl-5-(4-formylbenzyl) hydantoin

Product 1

HCID 127907633-n-Butyl-5-(4-cyanobenzyl) hydantoin

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The formyl compound (4.3 g., 0.01 mole), N,O-bis (trifluoroacetyl)hydroxylamine (3.6 g., 0.016 mole) and dry pyridine (2.6 ml. 0.032 mole) were mixed in benzene (75 ml) and heated under reflux for 2 hours. After cooling the benzene solution was washed with water (2×50 ml), dried over magnesium sulphate monohydrate and evaporated in vacuo to give an oil which slowly crystallised. This product was further purified by silica gel chromatography and recrystallisation from a small volume of ethyl acetate to give the title compound, yield 2.5 g., m.p. 136° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. washwas washed with water (2×50 ml)
  4. dry with materialdried over magnesium sulphate monohydrate
  5. customevaporated in vacuo
  6. customto give an oil which
  7. customslowly crystallised
  8. customThis product was further purified by silica gel chromatography and recrystallisation from a small volume of ethyl acetate

Sources & evidence

ORD record
ord-5572030541d544d6852e666020d13bb4
Source dataset
uspto-grants-1981_10
Patent number
US04293563

Reaction notes

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