Water → N-(2,3-dichloro-4-hydroxyphenyl)-3-chloro-2,2-dimethylpropane-carboxamide

HRID 583223Notes

Reaction equation

HRID 583223 reaction equation
Cl[CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([Cl:6])=O.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([Cl:17])[C:11]=1[Cl:18].O.[O:20]1CCC[CH2:21]1>>[Cl:18][C:11]1[C:12]([Cl:17])=[C:13]([OH:16])[CH:14]=[CH:15][C:10]=1[NH:9][C:21]([CH2:2][C:3]([CH3:8])([CH3:7])[CH2:4][Cl:6])=[O:20]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 98775294-Amino-2,3-dichlorophenol

Product 1

HCID 21311020N-(2,3-dichloro-4-hydroxyphenyl)-3-chloro-2,2-dimethylpropane-carboxamide

Procedure

1.55 g (0.01 mol) of chloropivaloyl chloride were added dropwise at 0° C. to a solution of 1.93 g (0.011 mol) of 4-amino-2,3-dichlorophenol in 30 ml of tetrahydrofuran, and stirring of the mixture was continued at 25° C. until starting compound was no longer detectable by thin-layer chromatography. The reaction mixture was subsequently poured into water and extracted three times using 20 ml of methylene chloride. The combined organic phases were washed twice using water, dried and concentrated. The residue was chroamtographed on silica gel (eluent: cyclohexane: ethyl acetate=2:1; yield: 0.75 g, m.p. 115° C.).

Workup

  1. customwas continued at 25° C.
  2. extractionextracted three times
  3. washThe combined organic phases were washed twice using water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e7f1a394f6f94d4cb2c89623189c4d6e
Source dataset
uspto-grants-1999_07
Patent number
US05929119

Reaction notes

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