Water → 2-[2-(2-Methoxyethoxy)-5-aminobenzenesulfonamido]-4-hexadecyloxy-5-methylphenol

HRID 1389901Notes

Reaction equation

HRID 1389901 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[S:15]([NH:18][C:19]1[CH:24]=[C:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:22]([CH3:42])=[CH:21][C:20]=1[OH:43])(=[O:17])=[O:16].[Cl-].[NH4+].O>[Fe].C(O)(C)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[S:15]([NH:18][C:19]1[CH:24]=[C:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:22]([CH3:42])=[CH:21][C:20]=1[OH:43])(=[O:16])=[O:17]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 127288472-[2'(2-Methoxyethoxy)-5'-nitrobenzenesulfonamido]-4-hexadecyloxy-5-methylphenol

Product 1

HCID 205128082-[2-(2-Methoxyethoxy)-5-aminobenzenesulfonamido]-4-hexadecyloxy-5-methylphenol

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Procedure

32 g of 2-[2'-(2-methoxyethoxy)-5'-nitrobenzenesulfonamido]-4-hexadecyloxy-5-methylphenol prepared as described in Step (b) above, 24 g of iron powder (Fe2O3), 12 g of Fe3O4, 0.6 g of ammonium chloride and 25 ml of water were added to 300 ml of isopropyl alcohol and the mixture was refluxed on a steam bath with stirring for 1 hour. After completion of the reaction, the mixture was filtered while hot and the filtrate was cooled with ice. The crystals thus-precipitated were recovered by filtration, washed with 50 ml of isopropyl alcohol and air-dried. Yield: 23 g; Melting Point: 142° to 144° C.

Workup

  1. temperaturethe mixture was refluxed on a steam bath
  2. customAfter completion of the reaction
  3. filtrationthe mixture was filtered while hot and the filtrate
  4. temperaturewas cooled with ice
  5. customThe crystals thus-precipitated
  6. filtrationwere recovered by filtration
  7. washwashed with 50 ml of isopropyl alcohol
  8. customair-dried

Sources & evidence

ORD record
ord-efa363b5940e44ecb795f9cb4fe11dc5
Source dataset
uspto-grants-1981_01
Patent number
US04246414

Reaction notes

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