Thionyl Chloride → HCID 21507698, compound

HRID 1287309Notes

Reaction equation

[CH2:1]([N:8]1[C:12]([CH2:13]O)=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:29])=O>C(Cl)(Cl)Cl.C(OC(C)C)(C)C>[CH2:1]([N:8]1[C:12]([CH2:13][Cl:29])=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -5 °C

Procedure

60 grams of 1-benzyl-3,4-diphenyl-5-hydroxymethylpyrazole dissolved in 150 ml of anhydrous chloroform are added to 51 ml of thionyl chloride dissolved in 450 ml of anhydrous chloroform, which has been cooled to -5° C. The solution is heated for 3 hours under reflux whilst being stirred. It is then cooled to ambient temperature and the chloroform is evapoated under reduced pressure. The residue is dissolved in 200 ml of petroleum ether and then suspended in 100 ml of diisopropyl ether. 53.4 grams of 1-benzyl-3,4-diphenyl-5-chloromethylpyrazole melting at 99° C are thus obtained.

Workup

temperatureThe solution is heated for 3 hours
temperatureunder reflux
temperatureIt is then cooled to ambient temperature

Sources & evidence

ORD record: ord-f8dbc7eb940846869c59852e9ff116d5
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03984431

Reaction notes

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