4-Chloroaniline → HCID 11624546, compound

HRID 971319Notes

Reaction equation

HRID 971319 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)=[O:12]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:21]([C:18]2[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][C:11]([O:10][CH3:9])=[O:12])=[CH:20][CH:19]=2)(=[O:23])=[O:22])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 23158517Methyl 3-[4-(chlorosulfonyl)phenyl]propanoate

Product 1

HCID 11624546HCID 11624546, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloroaniline (957 mg, 7.5 mmol) was dissolved in pyridine (25 mL). The resulting mixture was cooled down to 0° C. Methyl 3-(4-chlorosulphonyl)phenylpropionate (1.314 g, 5.0 mmol) was added in portions. The mixture was stirred between 0° C. and room temperature overnight. Solvents were evaporated to dryness. The crude oil was dissolved in ethyl acetate (30 mL) and washed with 10% HCl (2×15 mL) and brine (1×15 mL). Organic phase was dried over magnesium sulfate before filtering and removal of solvent. The desired product, e.g. methyl 3-{4-[(4-chloroanilino)sulfonyl]phenyl}propanoate (1.458 g, 82.4%), was obtained as a colorless solid, in 98.5% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. customSolvents were evaporated to dryness
  2. dissolutionThe crude oil was dissolved in ethyl acetate (30 mL)
  3. washwashed with 10% HCl (2×15 mL) and brine (1×15 mL)
  4. dry with materialOrganic phase was dried over magnesium sulfate
  5. filtrationbefore filtering
  6. customremoval of solvent

Sources & evidence

ORD record
ord-b2977a64be3f4952aa71b17bd0361b92
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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