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Ethylamine → N-ethyl-4-nitrobenzenesulfonamide

HRID 1176716
Notes
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Reaction equation

HRID 1176716 reaction equation
[CH2:1]([NH2:3])[CH3:2].[N+:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1)([O-:6])=[O:5]>O.CO>[CH2:1]([NH:3][S:13]([C:10]1[CH:9]=[CH:8][C:7]([N+:4]([O-:6])=[O:5])=[CH:12][CH:11]=1)(=[O:14])=[O:15])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6341EthylamineHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 232621N-ethyl-4-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

70% ethylamine in water (12.7 mL) and methanol (50 mL) are mixed. It is cooled to 0-5° C. 4-nitrobenzenesulfonyl chloride (10 g) is added portion-wise maintaining the temperature under 5° C. It is stirred for 15 minutes, maintaining the temperature, until the transformation is complete. Water (100 mL) is added. It is stirred for 30 minutes maintaining the temperature under 5° C. The reaction mixture is filtered, the isolated solid is washed with water and dried, obtaining 8.99 g of N-ethyl-4-nitrobenzene-sulfonamide.

Workup

  1. temperaturemaintaining the temperature under 5° C
  2. temperaturemaintaining the temperature
  3. stirringIt is stirred for 30 minutes
  4. temperaturemaintaining the temperature under 5° C
  5. filtrationThe reaction mixture is filtered
  6. washthe isolated solid is washed with water
  7. customdried

Sources & evidence

ORD record
ord-083790dad6ef4dba9d797a97649fae82
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842821B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes