Bromoform → HCID 18005401, compound

HRID 989238Notes

Reaction equation

HRID 989238 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:12]=[C:11]([C:26]#[N:27])[C:10]=1[S:28][CH2:29][CH3:30].C(Br)(Br)[Br:32]>>[Br:32][C:9]1[N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:12]=[C:11]([C:26]#[N:27])[C:10]=1[S:28][CH2:29][CH3:30]

Participants

4

Reactant 3

HCID 5558BromoformHCID 10906Tert-Butyl nitriteHCID 111117145-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(ethylthio)-1H-pyrazole-3-carbonitrile

Product 1

HCID 18005401HCID 18005401, compound

Conditions

Temperature
20 °C

Procedure

90% Tertiary-butyl nitrite (27.9 ml) was slowly added to a stirred solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile (49.8 g) in bromoform (600 ml) at 0-5° C. The mixture was stirred for three hours whilst warming to 20° C. evaporated and re-evaporated after addition of hexane/ethyl acetate (1:1) to give 5-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile (32.65 g), showing 93.3 area % purity by HPLC and with a retention time of 11.26 minutes on a 25.0 cm by 4.6 mm SUPELCOSIL LC-18 column, eluting with CH3CN/H2O (3:1) solvent at 1 ml/minute. By proceeding in a similar manner the following compound was prepared: 5-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylthio-1H-pyrazole-3-carbonitrile, m.p.134-140° C.

Workup

  1. customevaporated
  2. customre-evaporated
  3. additionafter addition of hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-966b12411fc04cea8532e02d0ec937b4
Source dataset
uspto-grants-2003_10
Patent number
US06638956B2

Reaction notes

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