Triethylamine → HCID 56981279, compound

HRID 1834219Notes

Reaction equation

HRID 1834219 reaction equation
[N+](C1C=C([O:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])C=CC=1N)([O-])=O.[N+:21]([C:24]1[CH:25]=[C:26](O)[CH:27]=[CH:28][C:29]=1[NH2:30])([O-:23])=[O:22].C(N(CC)CC)C>CC(C)=O>[N+:21]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=1[NH:30][O:11][S:12]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:14])=[O:13])([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 37588824-Amino-3-NitrophenolHCID 15585512HCID 15585512, compound

Product 1

HCID 56981279HCID 56981279, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

In order to prepare 2-nitro-4-phenylsulfonyloxy-aniline, 15.4 g of 3-nitro-4-amino-phenol in 100 ml of acetone were mixed with 14 ml of triethylamine, and 17.6 g of benzane-sulfonic acid-chloride dissolved in 30 ml of acetone were added dropwise, while stirring, at an internal temperature not exceeding 20° C in an ice bath. The mixture was continued to be stirred for another 3 hours at room temperature, the triethylamine-hydrochloride was filtered off, and the filtrate was evaporated to dryness. The residue was then stirred with 50 ml of methanol and was filtered. After washing with methanol and drying, 18.2 g of 2-nitro-phenylsulfonyloxy-aniline were obtained, which has a melting point of 140° C.

Workup

  1. additionwere added dropwise
  2. customexceeding 20° C in an ice bath
  3. stirringto be stirred for another 3 hours at room temperature
  4. filtrationthe triethylamine-hydrochloride was filtered off
  5. customthe filtrate was evaporated to dryness
  6. stirringThe residue was then stirred with 50 ml of methanol
  7. filtrationwas filtered
  8. washAfter washing with methanol
  9. customdrying

Sources & evidence

ORD record
ord-88d02beec9f34c3ca06eb77bf58cbe9f
Source dataset
uspto-grants-1978_01
Patent number
US04069325

Reaction notes

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