Hydrochloric Acid → HCID 17096642, compound

HRID 1287700Notes

Reaction equation

HRID 1287700 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:11]([O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18])[CH2:12][CH3:13].S(Cl)(Cl)=O.S(=O)=O.Cl>ClC1C=CC=CC=1>[CH2:11]([O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH:18][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1])[CH2:12][CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 83732-Methylbenzoic acidHCID 24386Thionyl ChlorideHCID 4274323-propoxyaniline

Product 1

HCID 17096642HCID 17096642, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A 13.6 g (0.1 mol) portion of o-methylbenzoic acid and 15.1 g (0.1 mol) of m-n-propoxy-aniline were dissolved in 100 ml of chlorobenzene. An 11.9 g (0.1 mol) amount of thionylchloride was added dropwise to the prepared solution at 40° - 50° C, and the mixture was stirred at 90° - 95° C for 4 hours, whereby sulfur dioxide and hydrogen chloride were continuously generated. After the reaction, the reaction mixture was poured into ice water and extracted with a mixture of benzene and hexane. The product was recrystallized from the mixed solvent to obtain 23.6 g (88%) of white needles having a melting point of 92° -94° C.

Workup

  1. customAfter the reaction
  2. extractionextracted with a mixture of benzene and hexane
  3. customThe product was recrystallized from the mixed solvent

Sources & evidence

ORD record
ord-6e8ff88f98414916ae847f5e35ca15f3
Source dataset
uspto-grants-1976_10
Patent number
US03985804

Reaction notes

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