4-Chlorobutyryl chloride → HCID 54349253, compound

HRID 1060489Notes

Reaction equation

HRID 1060489 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[Cl:12].CCN(C(C)C)C(C)C.[Cl:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:27](=[O:28])[CH2:26][CH2:25][CH2:24][Cl:23])=[CH:7][C:6]=1[Cl:12]

Participants

6

Reactant 3

HCID 783704-Chlorobutyryl chloride2×HCID 81531Diisopropylethylamine2×HCID 68819387HCID 68819387, compound

Product 1

HCID 54349253HCID 54349253, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-amino-2-chlorobenzoic acid methyl ester hydrochloride (0.52 g) and DIEA (0.27 mL) in CH2Cl2 (20 mL) at 0° C. under N2 was added 4-chlorobutyryl chloride (0.3 mL) and the mixture was stirred for 4 h at that temperature. DMAP (0.23 mmol) was added and the mixture was stirred at room temperature overnight. 4-Chlorobutyryl chloride (0.3 mL) and DIEA (0.09 mL) were added and the mixture was stirred for 24 h. The mixture was diluted with CH2Cl2 (100 mL) and the solution was washed successively with 1N HCl, std. NaHCO3, brine, dried and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 3:1) to yield 4-(4-chlorobutyryl)amino-2-chlorobenzoic acid methyl ester (0.64 g). ESMS: m/z 290 (MH+).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. stirringthe mixture was stirred for 24 h
  3. washthe solution was washed successively with 1N HCl, std
  4. dry with materialNaHCO3, brine, dried
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-554407d8f38042cc8d012a6bed9748df
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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