1,3-Dibromo-5,5-dimethylhydantoin → HCID 13911130, compound

HRID 2166681Notes

Reaction equation

HRID 2166681 reaction equation
[C:1]([O:4][C@@H:5]1[C@@:33]2([CH3:34])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:35])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:28])[CH2:18][CH2:19][CH2:20][C:21]([O:24][C:25](=[O:27])[CH3:26])([CH3:23])[CH3:22])[CH2:8][C@@H:7]([O:36][C:37](=[O:39])[CH3:38])[CH2:6]1)(=[O:3])[CH3:2].BrN1C(C)(C)C(=O)N(Br)C1=O.CC1C=C(C)N=C(C)C=1>CCCCCC.C1(C)C(C)=CC=CC=1.C(OC(=O)C)C>[C:1]([O:4][C@@H:5]1[C@@:33]2([CH3:34])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:35])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:28])[CH2:18][CH2:19][CH2:20][C:21]([O:24][C:25](=[O:27])[CH3:26])([CH3:22])[CH3:23])[CH2:8][C@@H:7]([O:36][C:37](=[O:39])[CH3:38])[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 79532,4,6-TrimethylpyridineHCID 53763193HCID 53763193, compound

Product 1

HCID 13911130HCID 13911130, compoundYield 87.3%

Reagents, catalysts & solvents 3

HCID 7237O-XyleneSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 1α,3β,25-triacetoxycholest-5-ene (544 mg, 1 m mole) in dry hexane (10 m), 1,3-dibromo-5,5-dimethylhydantoin (172 mg, 0.6 m moles) was added dropwise under stirring and heating at oil bath temperature of 95° C., and the mixture was continued to react under the irradiation of infrared rays for 15 minutes. The reaction mixture was cooled, and the resulting precipitate was removed by filtration, the filtrate was concentrated at reduced pressure at 40° C. to afford a residual product. Xylene was added to this substance to form a solution. The resulting solution was added dropwise to a solution held at 170° C. of s-collidine (2.5 ml) in dry xylene (3 ml), and the reaction was carried out for additional 20 minutes. After the reaction, the resulting precipitate was removed by filtration and the filtrate was concentrated under reduced pressure at 40° C. to give residual product. The product was dissolved in ethylacetate (20 ml). The ethylacetate solution was washed with 1 N hydrochloric acid (3×10 ml), saturated sodium bicarbonate and water, and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to give 473 mg of residual product.

Workup

  1. customto react under the irradiation of infrared rays for 15 minutes
  2. temperatureThe reaction mixture was cooled
  3. customthe resulting precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated at reduced pressure at 40° C.
  5. customto afford a residual product
  6. customto form a solution
  7. additionThe resulting solution was added dropwise to a solution
  8. customAfter the reaction
  9. customthe resulting precipitate was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure at 40° C.
  11. customto give residual product
  12. washThe ethylacetate solution was washed with 1 N hydrochloric acid (3×10 ml), saturated sodium bicarbonate and water
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe drying agent was removed by filtration
  15. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e6f0ee9a58d849fb8933e4da9288f445
Source dataset
uspto-grants-1983_06
Patent number
US04388243

Reaction notes

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