1,3-Dibromo-5,5-dimethylhydantoin → HCID 22823421, compound

HRID 2166683Notes

Reaction equation

HRID 2166683 reaction equation
[CH2:1]([O:3][C:4]([O:6][C@@H:7]1[C@@:37]2([CH3:38])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:32])[CH2:20][CH2:21][C@@H:22]([O:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:23]([CH3:25])[CH3:24])[CH2:10][C@@H:9]([O:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:8]1)=[O:5])[CH3:2].CCCCCC.BrN1C(C)(C)C(=O)N(Br)C1=O.CC1C=C(C)N=C(C)C=1>C1(C)C(C)=CC=CC=1.C(OC(=O)C)C>[CH2:1]([O:3][C:4]([O:6][C@@H:7]1[C@@:37]2([CH3:38])[C:11](=[CH:12][CH:13]=[C:14]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:32])[CH2:20][CH2:21][C@@H:22]([O:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:23]([CH3:25])[CH3:24])[CH2:10][C@@H:9]([O:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:8]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 79532,4,6-TrimethylpyridineHCID 8058HexaneHCID 22823420HCID 22823420, compound

Product 1

HCID 22823421HCID 22823421, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1α,3β,24(R)-triethoxycarbonyloxycholest-5-ene (3.49 g, 5.5 m moles), dry hexane (58 ml) and 1,3-dibromo-5,5-dimethylhydantoin (998 mg, 3.3 m moles) was boiled under the irradiation of infrared rays for 15 minutes. The reaction mixture was cooled, and the resulting 5,5-dimethylhydantoin and the excessive 1,3-dibromo-5,5-dimethylhydantoin were removed by filtration. The filtrate was concentrated at reduced pressure 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 170° C. of s-collidine (14.5 ml) in dry xylene (19 ml), and the reaction was carried out for additional 20 minutes. After the reaction, the hydrobromide of s-collidine was removed by filtration and the filtrate was concentrated under reduced pressure at 40° C. to give residual product. The residue was dissolved in ethylacetate (200 ml). The organic phase was washed with 1 N hydrochloric acid (3×10 ml), saturated sodium bicarbonate solution 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 3.68 g of residual product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe resulting 5,5-dimethylhydantoin and the excessive 1,3-dibromo-5,5-dimethylhydantoin were removed by filtration
  3. concentrationThe filtrate was concentrated at reduced pressure
  4. customto afford a residual product
  5. customto form a solution
  6. additionThe resulting solution was added dropwise to a solution
  7. customAfter the reaction
  8. customthe hydrobromide of s-collidine was removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure at 40° C.
  10. customto give residual product
  11. washThe organic phase was washed with 1 N hydrochloric acid (3×10 ml), saturated sodium bicarbonate solution and water
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe drying agent was removed by filtration
  14. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-30aa5547f50342dc92c957487758863e
Source dataset
uspto-grants-1983_06
Patent number
US04388243

Reaction notes

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