Thionyl Chloride → HCID 86737991, compound

HRID 1388082Notes

Reaction equation

HRID 1388082 reaction equation
S(Cl)(Cl)=O.[CH2:5]([CH:7]([NH:10][C:11]1[C:12]([N+:25]([O-:27])=[O:26])=[CH:13][C:14]([CH2:21][CH:22]=[N:23]O)=[C:15]([CH3:20])[C:16]=1[N+:17]([O-:19])=[O:18])[CH2:8][CH3:9])[CH3:6]>O1CCCC1>[CH2:5]([CH:7]([NH:10][C:11]1[C:12]([N+:25]([O-:27])=[O:26])=[CH:13][C:14]([CH2:21][C:22]#[N:23])=[C:15]([CH3:20])[C:16]=1[N+:17]([O-:19])=[O:18])[CH2:8][CH3:9])[CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86737992HCID 86737992, compound

Product 1

HCID 86737991HCID 86737991, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of thionyl chloride (25.0 ml) in tetrahydrofuran (THF; 100 ml) is added at <20° C. to a solution of {5-[(1-ethylpropyl)amino]-4,6-dinitro-o-tolyl}acetaldehyde oxime (12.0 g; 0.037 mol) in THF (160 ml). The reaction mixture is stirred overnight at room temperature, filtered, and the filtrate concentrated in vacuo to leave an oil which crystallizes, when seeded, to afford the title product (9.8 g), an orange solid. A sample is purified for analysis, melting point 59°-60° C.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto leave an oil which
  4. customcrystallizes

Sources & evidence

ORD record
ord-ac4103b6bd84487d94d03d3db9ad6b24
Source dataset
uspto-grants-1984_02
Patent number
US04430114

Reaction notes

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