N-bromobutanimide → HCID 13728613, compound

HRID 986754Notes

Reaction equation

HRID 986754 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]=[C:10]([C:13]#[N:14])[C:9](=[O:15])[C:8]=2[CH:16]=1)([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:17][C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]=[C:10]([C:13]#[N:14])[C:9](=[O:15])[C:8]=2[CH:16]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 7360173-Cyano-6-isopropylchromone

Product 1

HCID 13728613HCID 13728613, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In carbon tetrachloride (300 ml) was suspended 6-isopropyl-4-oxo-4H-1-benzopyran-3-carbonitrile (10.65 g). To the suspension was added N-bromosuccinimide (8.90 g). The mixture was subjected to reflux for two hours under irradiation of infrared ray lamp (Toshiba, 100 V, 375 WR). The resultant was then cooled to room temperature, followed by removal of insolubles by filtration. The filtrate was concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate (150 ml), which was washed with water three times, dried and concentrated. The precipitating crystals were collected by filtration to give 6-(1-bromo-1-methylethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile as colorless prisms (7.0 g). Melting point: 115°-117° C.

Workup

  1. temperatureto reflux for two hours under irradiation of infrared ray lamp (Toshiba, 100 V, 375 WR)
  2. customfollowed by removal of insolubles by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionThe concentrate was dissolved in ethyl acetate (150 ml)
  5. washwhich was washed with water three times
  6. customdried
  7. concentrationconcentrated
  8. filtrationThe precipitating crystals were collected by filtration

Sources & evidence

ORD record
ord-fd91f2272184463b9bf299769a58a621
Source dataset
uspto-grants-1987_12
Patent number
US04716167

Reaction notes

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