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

HRID 1164242Notes

Reaction equation

HRID 1164242 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([N+]([O-])=O)=[CH:10][CH:9]=[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].C(O)(C)C.[Cl-].[NH4+:49]>[Fe].[O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+2].[Fe+2].O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:49])=[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

7

Reactant 3

HCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 20512803HCID 20512803, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 21256123HCID 21256123, compoundCatalystHCID 962WaterSolvent

Procedure

32 g of 2-[2'-(2-methoxyethoxy)nitrobenzenesulfonamido]-4-hexadecyloxy-5-methylphenol was added to 300 ml of isopropyl alcohol together with 24 g of iron dust, 12 g of tri-iron tetroxide, 0.6 g of ammonium chloride, and 25 ml of water, and refluxed for 1 hour on a steam bath under stirring. After completion of the stirring, the mixture was hot-filtered and, after cooling the mother liquor, crystals thus formed were collected by filtration, washed with 50 ml of isopropyl alcohol, and air-dried. Yield: 23 g; m.p. 142° to 144° C.

Workup

  1. temperaturerefluxed for 1 hour on a steam bath
  2. filtrationAfter completion of the stirring, the mixture was hot-filtered
  3. temperatureafter cooling the mother liquor, crystals
  4. customthus formed
  5. filtrationwere collected by filtration
  6. washwashed with 50 ml of isopropyl alcohol
  7. customair-dried

Sources & evidence

ORD record
ord-b0f4c8eb813847edbb00a044028512b9
Source dataset
uspto-grants-1983_01
Patent number
US04368251

Reaction notes

Loading…