Hydrochloric Acid → HCID 53816685, compound

HRID 1277357Notes

Reaction equation

HRID 1277357 reaction equation
[N:1]1([CH:6]([CH:16](O)[C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.Cl>N1C=CC=CC=1>[N:1]1([C:6](=[CH:16][C:17](=[O:22])[C:18]([CH3:20])([CH3:19])[CH3:21])[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 23453636HCID 23453636, compound

Product 1

HCID 53816685HCID 53816685, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product (4.9 g, 0.015 mol) of Stage 1 and p-toluenesulphonyl chloride (3.0 g, 0.06 mol) were mixed together in pyridine (50 ml) at 20°. After standing at room temperature for 48 hours, the solution was poured into crushed ice (50 ml)/concentrated hydrochloric acid (50 ml). The mixture was extracted with diethyl ether (100 ml), and the extract washed with water (3×100 ml) and dried over anhydrous sodiumsulphate. Removal of the ether gave a brown gum which was further purified by column chromatography (silica gel eluted with diethyl ether) to give 2-(1,2,4-triazol-1-yl)-1-p-chlorophenyl-5,5-dimethyl-hex-2-en-1,4-dione asa gum (2.8 g; yield 60%).

Workup

  1. additionthe solution was poured
  2. extractionThe mixture was extracted with diethyl ether (100 ml)
  3. washthe extract washed with water (3×100 ml)
  4. dry with materialdried over anhydrous sodiumsulphate
  5. customRemoval of the ether
  6. customgave a brown gum which
  7. customwas further purified by column chromatography (silica gel eluted with diethyl ether)

Sources & evidence

ORD record
ord-15dfeb2ab5d24ffaa9fe0682a383c692
Source dataset
uspto-grants-1981_07
Patent number
US04277469

Reaction notes

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