Chloroacetyl chloride → 2-chloro-N-(2,4-dihydroxyphenyl)acetamide

HRID 1925351Notes

Reaction equation

HRID 1925351 reaction equation
Cl.[NH2:2][C:3]1[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][C:4]=1[OH:10].[Cl:11][CH2:12][C:13](Cl)=[O:14]>C(Cl)Cl>[Cl:11][CH2:12][C:13]([NH:2][C:3]1[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][C:4]=1[OH:10])=[O:14]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 134088224-Aminobenzene-1,3-diol hydrochloride

Product 1

HCID 529048732-chloro-N-(2,4-dihydroxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-aminoresorcinol hydrochloride (30 g, 0.1857 mol) in CH2Cl2, (460 mL) TEA (77.6 mL, 0.557 mol) was added at 0° C. To the resulting mixture, chloroacetyl chloride (14.78 mL, 0.1857 mol) was added drop wise and the solution was stirred for 60 h at RT. The crude product was washed through a plug of silica gel with CH2Cl2 and purified through column chromatography using 100% CH2Cl2→25%→50%→75% 90:10:1 CH2Cl2:MeOH:NH4OH. The solution was concentrated in vacuo to give the title compound. MS (ESI, pos. ion) m/z: 202 (M+1). Mass calc'd for C8H8ClNO3: 201.02.

Workup

  1. washThe crude product was washed through a plug of silica gel with CH2Cl2
  2. custompurified through column chromatography
  3. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-ec7b08a68a23427fa02d03c4f7fffa9b
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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