Thionyl Chloride → HCID 21242580, compound

HRID 26118Notes

Reaction equation

HRID 26118 reaction equation
[CH3:1][C:2]1[CH:6]([N:7]=[N:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:5](=[O:15])[N:4]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=O)=[O:23])=[CH:18][CH:17]=2)[N:3]=1.O=S(Cl)[Cl:28]>CN(C)C=O>[Cl:28][S:22]([C:19]1[CH:20]=[CH:21][C:16]([N:4]2[C:5](=[O:15])[CH:6]([N:7]=[N:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[C:2]([CH3:1])=[N:3]2)=[CH:17][CH:18]=1)(=[O:25])=[O:23]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 203940703-Methyl-4-(2-pyridylazo)-1-(p-sulfophenyl)-2-pyrazolin-5-one

Product 1

HCID 21242580HCID 21242580, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.0 g (0.025 mole) of 3-methyl-4-(2-pyridylazo)-1-(p-sulfophenyl)-2-pyrazolin-5-one was added in portions with stirring to 70 ml of SOCl2. To this suspension was added dropwise 3 ml of dimethylformamide. The mixture was stirred overnight. The resulting solution was poured slowly with vigorous stirring into 500 ml of ice water. The solid product was filtered and pressed dry. This product was slurried in 50 percent tetrahydrofuran/ethyl ether, filtered, and dried to obtain 5.3 g (56 percent) of orange solid.

Workup

  1. additionThe resulting solution was poured slowly
  2. filtrationThe solid product was filtered
  3. custompressed dry
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-9d8bb2789cc347999019fe8bb49d8242
Source dataset
uspto-grants-1979_04
Patent number
US04148641

Reaction notes

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