Toluene → HCID 178443319, compound

HRID 1378283Notes

Reaction equation

HRID 1378283 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([S:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].CO[C:26](OC)(OC)[CH2:27][C:28]([O:30]CC)=O.C1(C)C=CC=CC=1.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([NH:51][NH2:52])=[CH:47][CH:46]=1>S(=O)(=O)(O)O.C(O)(=O)C>[Cl:1][C:2]1[CH:8]=[C:7]([S:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:26]1[CH2:27][C:28](=[O:30])[N:51]([C:48]2[CH:49]=[CH:50][C:45]([Cl:44])=[CH:46][CH:47]=2)[N:52]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 70624(4-Chlorophenyl)hydrazineHCID 108613032-Chloro-4-dodecylsulfonylanilineHCID 19938995HCID 19938995, compound

Product 1

HCID 178443319HCID 178443319, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A stirred mixture of 2-chloro- 4-dodecylsulfonylaniline (21.9 g, 0.061 moles), ethyl 3,3,3-trimethoxypropionate (11.7 g, 0.061 moles) and toluene (100 ml) was heated in an oil-bath at 110° C. until solution was attained. Concentrated sulfuric acid (4 drops) was added and the stirred mixture was heated for 2-25 hours allowing volatiles to distill off. The solution was cooled and the solvent was removed on the rotavapor to leave an oil. The oil was dissolved in glacial acetic acid (100 ml) and 4-chlorophenylhydrazine (8.7 g, 0.061 moles) was added. The mixture was stirred at room temperature for 22 hours. Then the resulting solid was filtered off, washed with methanol and dried. The solid was purified by trituration with ethyl acetate to give the product as a pale yellow solid weighing 20.1 g (60%).

Workup

  1. temperaturethe stirred mixture was heated for 2-25 hours
  2. distillationto distill off
  3. temperatureThe solution was cooled
  4. customthe solvent was removed on the rotavapor
  5. customto leave an oil
  6. filtrationThen the resulting solid was filtered off
  7. washwashed with methanol
  8. customdried
  9. customThe solid was purified by trituration with ethyl acetate

Sources & evidence

ORD record
ord-0e43ab36f34b42e08e65d77367c0b4c4
Source dataset
uspto-grants-1997_09
Patent number
US05667946

Reaction notes

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