2,6-Dichlorobenzoyl chloride → Methyl 2-[(2,6-dichlorobenzoyl)amino]-3-(4-nitrophenyl)propanoate

HRID 1869784Notes

Reaction equation

HRID 1869784 reaction equation
[NH2:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:19]=1[C:20](Cl)=[O:21].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:19]=1[C:20]([NH:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4])=[O:21]

Participants

5

Reactant 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 81531Diisopropylethylamine2×HCID 560520Methyl 2-amino-3-(4-nitrophenyl)propanoate

Product 1

HCID 57987623Methyl 2-[(2,6-dichlorobenzoyl)amino]-3-(4-nitrophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 2-amino-3-(4-nitrophenyl)propanoate 2 (9.5 g) in CH2Cl2 (40 ml) is added, at 0° C., 2,6-dichlorobenzoyl chloride (7.71 g) dissolved in CH2Cl2 (40 ml). DIPEA (2 equ.) is then added dropwise to the mixture at 0° C. The reaction is then risen at RT and pH is brought to 7-8 by addition of DIPEA. The mixture is stirred for 2 h, then evaporated and the residue is placed in AcOEt (175 ml). The organic phase is washed one time with 5% NaHCO3 (150 ml), one time with water, one time with 10% KHSO4 (150 ml) and one time with brine, dried over MgSO4 and evaporated. No further purification is needed.

Workup

  1. customis then risen at RT
  2. customevaporated
  3. washThe organic phase is washed one time with 5% NaHCO3 (150 ml), one time with water, one time with 10% KHSO4 (150 ml) and one time with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customNo further purification

Sources & evidence

ORD record
ord-d9e91413bfb446a885e479e534906011
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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