Thionyl Chloride → HCID 67271754, compound

HRID 1696486Notes

Reaction equation

HRID 1696486 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH2:17]O)[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:5]=[C:4]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:3]=1.O=S(Cl)[Cl:25]>C1COCC1>[C:19]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([C:7]2[CH:8]=[C:9]([CH2:17][Cl:25])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:16]=2)[N:5]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67271645HCID 67271645, compound

Product 1

HCID 67271754HCID 67271754, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [3-(5-amino-3-t-butyl-pyrazol-1-yl)naphthalen-1-yl]methanol (1.6 g, 5.4 mmol) in THF (20 mL) was added SOCl2 (3.0 g, 25 mmol). The mixture was heated at reflux for 3 h and then concentrated under pressure to yield crude 3-t-butyl-1-[4-(chloromethyl)naphthalen-2-yl]-1H-pyrazol-5-amine (1.5 g), which was used for the next reaction without further purification. MS (ESI) m/z: 314 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated under pressure

Sources & evidence

ORD record
ord-75eebecdd0c04c29a593cfaa0f3beeda
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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