Diiodomethane → HCID 18326232, compound

HRID 1250436Notes

Reaction equation

HRID 1250436 reaction equation
N(OCCC(C)C)=O.N[C:10]1[C:11]([Cl:26])=[CH:12][C:13]([F:25])=[C:14]([C:16]2[C:20]([CH3:21])=[C:19]([C:22]#[N:23])[N:18]([CH3:24])[N:17]=2)[CH:15]=1.[I:27]CI>>[Cl:26][C:11]1[C:10]([I:27])=[CH:15][C:14]([C:16]2[C:20]([CH3:21])=[C:19]([C:22]#[N:23])[N:18]([CH3:24])[N:17]=2)=[C:13]([F:25])[CH:12]=1

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 17763650HCID 17763650, compound

Product 1

HCID 18326232HCID 18326232, compound

Conditions

Temperature
22 °C

Procedure

5.86 g of isoamyl nitrite are added dropwise at a temperature of below 15° C. to a solution of 2.64 g of 3-(5-amino-4-chloro-2-fluoro-phenyl)-4-methyl-5-cyano-1-methyl-[1H]-pyrazole in 54 g (16 ml) of diiodomethane. The reaction mixture is stirred for 14 hours at 22° C., and excess diiodomethane is evaporated in vacuo. All the diiodomethane is subsequently distilled off at 70-75° C./14 torr, and the crude product is purified over a silica gel column (eluent: ethyl acetate/hexane 1/5). The desired product is obtained in a yield of 1.88 g (50.2% of theory).

Workup

  1. customexcess diiodomethane is evaporated in vacuo
  2. distillationAll the diiodomethane is subsequently distilled off at 70-75° C./14 torr
  3. customthe crude product is purified over a silica gel column (eluent: ethyl acetate/hexane 1/5)

Sources & evidence

ORD record
ord-c2e2f7b0070748bd806fd613d8a9e177
Source dataset
uspto-grants-2002_01
Patent number
US06339046B1

Reaction notes

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