Tert-Butylamine → methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoate

HRID 581662Notes

Reaction equation

HRID 581662 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].Cl[S:7]([C:10]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:9])=[O:8]>C(OCC)(=O)C>[C:1]([NH:5][S:7]([C:10]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:8])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 15240541Methyl 2-(chlorosulfonyl)-4-nitrobenzoate

Product 1

HCID 15240542methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

206 g of tert-butylamine are added dropwise to a solution of 384 g of methyl 2-chlorosulfonyl-4-nitro-benzoate (Example b) in 1500 ml of ethyl acetate at 0° C. The reaction mixture is then allowed to warm up to room temperature and is stirred at this temperature for 1 hour. After washing with dilute hydrochloric acid and water, the organic phase is dried over MgSO4 and concentrated. The residue is extracted by stirring with diisopropyl ether; Yield of sulfonamide: 377.6 g; m.p.: 122-124° C.

Workup

  1. washAfter washing with dilute hydrochloric acid and water
  2. dry with materialthe organic phase is dried over MgSO4
  3. concentrationconcentrated
  4. extractionThe residue is extracted
  5. stirringby stirring with diisopropyl ether

Sources & evidence

ORD record
ord-d692b5868745437ea0fc3af6e425a959
Source dataset
uspto-grants-1999_07
Patent number
US05922646

Reaction notes

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