Carbon Tetrachloride → HCID 68121707, compound

HRID 972321Notes

Reaction equation

HRID 972321 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([C:12]1[C:13]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:14][C:15]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][C:17]=1[CH3:18])(=[O:11])[CH3:10].C(Cl)(Cl)(Cl)Cl>C(O)C>[C:9]([C:12]1[C:13]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:14][C:15]([NH:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[C:16]([Br:1])[C:17]=1[CH3:18])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 940052,6-Bis(tert-butylamino)-4-methylpyridin-3-yl methyl ketone2×

Product 1

HCID 68121707HCID 68121707, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

534 mg. (3 mmol.) of N-bromosuccinimide (recrystallized from water) were added in small portions to a solution of 831 mg. (3 mmol.) of 3-acetyl-2,6-di-t-butylamino-4-methylpyridine (Compound V) in 20 ml. of carbon tetrachloride and 5 ml. of ethanol, and the reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was evaporated down at reduced pressure, and the residue was partitioned between ether and water. The organic phase was dried over anhydrous sodium sulfate and evaporated at reduced pressure to obtain yellow crystals. Recrystallization from methanol/water gave the product (990 mg.), m.p. 99°-100° C.

Workup

  1. customThe reaction mixture was evaporated down at reduced pressure
  2. customthe residue was partitioned between ether and water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customevaporated at reduced pressure
  5. customto obtain yellow crystals
  6. customRecrystallization from methanol/water
  7. customgave the product (990 mg.), m.p. 99°-100° C.

Sources & evidence

ORD record
ord-722d30080ad3412a995daec9ac3fd474
Source dataset
uspto-grants-1977_10
Patent number
US04052510

Reaction notes

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