Pyridine → 6-[alpha-(beta-Chloropropanamido)acetamido]-2,4-dichloro-3-methylphenol

HRID 1263065Notes

Reaction equation

HRID 1263065 reaction equation
[Cl:1][CH:2]([CH3:10])[C:3]([NH:5][CH2:6][C:7]([OH:9])=O)=[O:4].Cl.[NH2:12][C:13]1[C:18]([OH:19])=[C:17]([Cl:20])[C:16]([CH3:21])=[C:15]([Cl:22])[CH:14]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>O.C(#N)C>[Cl:1][CH:2]([CH3:10])[C:3]([NH:5][CH2:6][C:7]([NH:12][C:13]1[C:18]([OH:19])=[C:17]([Cl:20])[C:16]([CH3:21])=[C:15]([Cl:22])[CH:14]=1)=[O:9])=[O:4]

Participants

7

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 1702236-Amino-2,4-dichloro-m-cresol hydrochlorideHCID 20455717N-(2-Chloropropanoyl)glycine

Product 1

HCID 204557166-[alpha-(beta-Chloropropanamido)acetamido]-2,4-dichloro-3-methylphenolYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture composed of 158 g (0.96 mol) of N-(β-chloropropanoyl)glycine thus obtained and 92 g (0.4 mol) of 6-amino-2,4-dichloro-3-methylphenol hydrochloride were added 228 ml (2.88 mol) of pyridine and 2 liters of acetonitrile and stirred under cooling. To the solution was added dropwise 95.2 g (0.8 mol) of thionyl chloride. After the completion of the reaction, water was added to the reaction solution and the crystals thus deposited were collected by filtration and recrystallized from acetonitrile to obtain 125.2 g of 6-[α-(β-chloropropanamido)acetamido]-2,4-dichloro-3-methylphenol.

Workup

  1. customthus obtained
  2. temperatureunder cooling
  3. additionwas added to the reaction solution
  4. filtrationthe crystals thus deposited were collected by filtration
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-5acdb209e07c4f12aa06d379c57af99f
Source dataset
uspto-grants-1984_06
Patent number
US04455366

Reaction notes

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