Methyl malonyl chloride → HCID 86682941, compound

HRID 1497074Notes

Reaction equation

HRID 1497074 reaction equation
Cl[C:2](=[O:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[NH2:9][C:10]1[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19]>C(Cl)Cl>[CH3:7][O:6][C:4](=[O:5])[CH2:3][C:2]([NH:9][C:10]1[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=1[C:18](=[O:19])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:8]

Participants

4

Reactant 2

HCID 123460Methyl malonyl chlorideHCID 12516780(2-Amino-3,5-dichlorophenyl)(phenyl)methanone

Product 1

HCID 86682941HCID 86682941, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-chloro-3-oxopropanoate (317 mg, 249 μl, 2.25 mmol, Eq: 1.2) was added dropwise to a yellow solution of (2-amino-3,5-dichloro-phenyl)-phenyl-methanone (500 mg, 1.88 mmol, Eq: 1.00) in DCM (5 ml) at 0° C. The yellow solution was then allowed to warm slowly to RT. After completion of the reaction the mixture was washed with sat. NaHCO3 solution and brine, dried with Na2SO4 and evaporated. The remaining light brown residue (603 mg) was used in the next reaction step without further purification. MS (ESI): 366.0 (M+H)+.

Workup

  1. customAfter completion of the reaction the mixture
  2. washwas washed with sat. NaHCO3 solution and brine
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe remaining light brown residue (603 mg) was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-998d4d5658704a9da0232698b0de309b
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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