Tert-Butyl nitrite → HCID 18689526, compound

HRID 1871874Notes

Reaction equation

HRID 1871874 reaction equation
[Br:1]Br.N[C:4]1[N:8]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[C:11]([Cl:20])[N:10]=2)[N:7]=[CH:6][C:5]=1[C:21]#[N:22].N(OC(C)(C)C)=O>C(Cl)(Cl)Cl>[Br:1][C:4]1[N:8]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[C:11]([Cl:20])[N:10]=2)[N:7]=[CH:6][C:5]=1[C:21]#[N:22]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 24408BromineHCID 18689500HCID 18689500, compound

Product 1

HCID 18689526HCID 18689526, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10.7 g (0.0667 mol) of bromine were added at 25° C. with stirring in the course of 10 minutes to 9.3 g (0.029 mol) of the compound from Example 3 in 200 ml of chloroform; 4.5 g [0.0435 mol] of tert-butyl nitrite were then added in the course of 5 minutes at the same temperature and the mixture was subsequently stirred for 14 hours. The reaction solution was stirred into 1 l of ice water and then extracted with methylene chloride. The organic extract was washed in the customary manner and dried, filtered off with suction through neutral alumina and concentrated under reduced pressure. After triturating in ether/pentane, filtering off with suction and drying, 4.0 9 (35.7% of theory) of the title compound of m.p. 121-122° C. were obtained (Active Compound Example No. 2a.022).

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe organic extract
  3. washwas washed in the customary manner
  4. customdried
  5. filtrationfiltered off with suction through neutral alumina
  6. concentrationconcentrated under reduced pressure
  7. customAfter triturating in ether/pentane
  8. filtrationfiltering off with suction
  9. customdrying

Sources & evidence

ORD record
ord-44a42698243a4458997d6c2a36b2a493
Source dataset
uspto-grants-2000_08
Patent number
US06107253

Reaction notes

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