Water → HCID 54281195, compound

HRID 2286257Notes

Reaction equation

HRID 2286257 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[OH:12].[CH2:13]([S:25]([NH:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32])(=[O:27])=[O:26])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[Cl-].[NH4+].O>C(#N)C.C(O)(C)C>[NH2:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]([NH:1][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=2[NH:28][S:25]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:27])=[O:26])=[C:3]([OH:12])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 38948482-Amino-4-chloro-5-nitrophenolHCID 537176822-[(Dodecane-1-sulfonyl)amino]benzoyl chloride

Product 1

HCID 54281195HCID 54281195, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

28.2 g of 2-amino-4-chloro-5-nitrophenol was refluxed in 150 ml of acetonitrile and to the mixture, a solution containing 52.7 g of 2-dodecansulfonamidobenzoyl chloride obtained in Step (i) above dissolved in 50 ml of acetonitrile was added. After refluxing for 4 hours, the reaction mixture was cooled to deposit crystals. The crystals were collected by filtration, washed with acetonitrile, and dried to yield 56 g thereof. These crystals were refluxed with stirring for 1 hour together with 60 g of reduced iron powder, 2 g of ammonium chloride, 50 ml of water, and 500 ml of isopropanol. After removing the iron powder by filtration, the filtrate was poured into 2 liters of water to deposit crystals. The crystals were collected by filtration and recrystallized from acetonitrile to obtain 36 g of the 5-amino-4-chloro-2-(2-dodecansulfonamidobenzoylamino)phenol compound.

Workup

  1. additionwas added
  2. temperatureAfter refluxing for 4 hours
  3. temperaturethe reaction mixture was cooled
  4. filtrationThe crystals were collected by filtration
  5. washwashed with acetonitrile
  6. customdried
  7. customto yield 56 g
  8. temperatureThese crystals were refluxed
  9. customAfter removing the iron powder
  10. filtrationby filtration
  11. additionthe filtrate was poured into 2 liters of water
  12. filtrationThe crystals were collected by filtration
  13. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-029d46d3c2d743c883da3a47ab651fb7
Source dataset
uspto-grants-1982_04
Patent number
US04327173

Reaction notes

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