Water → HCID 18005393, compound

HRID 2301384Notes

Reaction equation

HRID 2301384 reaction equation
BrBr.[S-:3][C:4]#[N:5].[Na+].[NH2:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[Cl:23])[N:11]=[C:10]([C:24]#[N:25])[CH:9]=1.O>CO>[NH2:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][C:14]=2[Cl:23])[N:11]=[C:10]([C:24]#[N:25])[C:9]=1[S:3][C:4]#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 516871Sodium thiocyanateHCID 15869735HCID 15869735, compound

Product 1

HCID 18005393HCID 18005393, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

Bromine (0.5 ml) was added over 10 minutes to a stirred solution of sodium thiocyanate (1.7 g) in anhydrous methanol at −65° C. A solution of 5-amino-1-(2-chloro-4-(trifluoromethyl)phenyl]-1-H-pyrazole-3-carbonitrile (1.5 g) in anhydrous methanol was added over 10-minutes and the stirred mixture allowed to warm to 20° C. over 16-hours. After pouring into water the precipitate was collected and dried to give 5-amino-1-[2-chloro-4-(trifluoromethyl)phenyl]-4-thiocyanato-1H-pyrazole-3-carbonitrile (1.64 g). HPLC (C-18 column, eluting with 3:1 CH3CN/H2O at 1.0 ml/min.) showed the compound as a peak of 86.6% area at 5.11 minutes.

Workup

  1. customwas collected
  2. customdried

Sources & evidence

ORD record
ord-9a2f8d691e7045b58b092a29ede703a9
Source dataset
uspto-grants-2002_12
Patent number
US06500850B2

Reaction notes

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