Potassium Bromide → HCID 20394592, compound

HRID 614994Notes

Reaction equation

HRID 614994 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([S:15][CH3:16])=[N:13][CH2:14][CH:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:6]=2[CH:24]=1.[K+].[Br-]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([S:15][CH3:16])=[N:13][CH:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:6]=2[CH:24]=1

Participants

5

Reactant 2

HCID 253877Potassium BromideHCID 20394578HCID 20394578, compound

Product 1

HCID 20394592HCID 20394592, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2.8 g (7.8 mmol) of the end product of Example 24 and 13 g of activated manganese dioxide in 500 ml of toluene was refluxed overnight. The mixture was filtered through Celite, evaporated in vacuo and the residue treated with ether-petroleum ether to give a tan solid. Recrystallization from methylene chloride-ether gave a white powder, mp 180°-181°: Ir (KBr) 1610 and 1480 cm-1 ; nmr (CDCl3) 2.60 δ (s, 3H), 4.10 (d, J=12Hz, 1H) 5.20 (d, J=12Hz, 1H) and 6.90-7.80 (m, aromatic, 8H); uv λ max 219 nm (ε=36500), infl. 242 (19900) and 270 (8700); mass spectrum m/e 357 (M+).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe mixture was filtered through Celite
  3. customevaporated in vacuo
  4. additionthe residue treated with ether-petroleum ether
  5. customto give a tan solid
  6. customRecrystallization from methylene chloride-ether
  7. customgave a white powder, mp 180°-181°

Sources & evidence

ORD record
ord-4d2085fc75a640d8a53a185774d9a5d4
Source dataset
uspto-grants-1979_03
Patent number
US04146722

Reaction notes

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