Chloroform → HCID 13985228, compound

HRID 256144Notes

Reaction equation

HRID 256144 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH3:14])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].FC(F)(F)C(O)=[O:18].ClC1C=CC=C(C(OO)=O)C=1.C(Cl)(Cl)Cl>C(Cl)Cl>[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([S:11]([CH2:12][CH2:13][CH3:14])=[O:18])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 70297m-Chloroperbenzoic acidHCID 643320Benzenamine, 2-nitro-5-(propylthio)-

Product 1

HCID 13985228HCID 13985228, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Cool to 0°-5° C. a stirred solution of 2-nitro-5-propylthioaniline (21.2 g) in methylene chloride (350 ml) and add trifluoroacetic acid (11.40 g), followed by the dropwise addition of 85% m-chloroperbenzoic acid (22.34 g) in methylene chloride (450 ml). Stir 30 minutes at 0° C., then warm to room temperature and stir 3.5 hours. Add chloroform to dissolve the solids, and extract the mixture with 10% sodium carbonate solution three times, extract with water once, filter over magnesium sulfate, then evaporate the organic solvent in vacuo. Recrystallize the residue from methanol to obtain 2-nitro-5-propylsulfinylaniline, m.p. 128°-130° C.

Workup

  1. temperaturewarm to room temperature
  2. stirringstir 3.5 hours
  3. extractionextract the mixture with 10% sodium carbonate solution three times
  4. extractionextract with water once
  5. filtrationfilter over magnesium sulfate
  6. customevaporate the organic solvent in vacuo
  7. customRecrystallize the residue from methanol

Sources & evidence

ORD record
ord-51c22d78e8c1491489f712991104dd95
Source dataset
uspto-grants-1987_10
Patent number
US04701447

Reaction notes

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