3,4-Dichloroaniline → HCID 59809613, compound

HRID 2114375Notes

Reaction equation

HRID 2114375 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[CH2:10]([O:12][C:13](=[O:18])[C:14](Br)([CH3:16])[CH3:15])[CH3:11].C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:14]([CH3:16])([C:13]([O:12][CH2:10][CH3:11])=[O:18])[CH3:15])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 72573,4-DichloroanilineHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 59809613HCID 59809613, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A 15-mL sealed tube equipped with a magnetic stirring bar was charged with 3,4-dichloroaniline (1.63 g, 10.0 mmol) and treated with ethyl-2-bromoisobutyrate (1.6 mL, 11 mmol), diisopropylethylamine (1.9 mL, 11.0 mmol), and NaT (824 mg, 0.600 mmol). The vessel was sealed tightly, heated to 110° C. and maintained at that temperature for 48 h. After allowing the reaction mixture to cool to room temperature, the reaction was diluted with THF and the solids were filtered off. The filtrate was collected and concentrated under vacuum. The crude oil was purified by silica gel chromatography (35 g Redisep column, silica 40 um, 35 mL/min, A: CH2Cl2, B: MeOH, B: 0% for 20 min, 5% for 5 min, 10% for 5 min; detection at 214 nm) to give 1.71 g (55%) of ethyl N-(3,4-dichlorophenyl)-2-methylalaninate as a brown oil. MS (ES) m/z 276 [M+H]+

Workup

  1. customA 15-mL sealed tube
  2. customequipped with a magnetic stirring bar
  3. customThe vessel was sealed tightly
  4. temperaturemaintained at that temperature for 48 h
  5. temperatureto cool to room temperature
  6. filtrationthe solids were filtered off
  7. customThe filtrate was collected
  8. concentrationconcentrated under vacuum
  9. customThe crude oil was purified by silica gel chromatography (35 g Redisep column, silica 40 um, 35 mL/min
  10. wait5% for 5 min
  11. wait10% for 5 min

Sources & evidence

ORD record
ord-36c045779a0744c5bcd7348d3e2894e5
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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