Dichloromethane → Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-aminophenoxy)-3-chlorophenyl)acetate

HRID 1927730Notes

Reaction equation

HRID 1927730 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:29]=[CH:28][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]=3[Cl:27])=[C:13]([N+:30]([O-])=O)[CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[NH4+].[Cl-].C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:29]=[CH:28][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]=3[Cl:27])=[C:13]([NH2:30])[CH:12]=2)=[O:10])=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 68468998Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-3-chlorophenyl)acetate

Product 1

HCID 68467172Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-aminophenoxy)-3-chlorophenyl)acetateYield 98.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-3-chlorophenyl)acetate (110 mg, 0.219 mmol) was diluted with THF (1 mL) followed by the addition of Zn dust (14.3 mg, 0.219 mmol) and saturated NH4Cl (1 mL). After stirring for 1 hour, the reaction was diluted DCM and 10% aq. sodium carbonate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-aminophenoxy)-3-chlorophenyl)acetate (102 mg, 98.6% yield).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-272fdfe595ea459aaed3f3e71973003c
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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