Pyridine → 5-Formyl-3-(methylamino)-2-phenoxybenzene-1-sulfonamide

HRID 1390055Notes

Reaction equation

HRID 1390055 reaction equation
N1C=CC=CC=1.C(Cl)Cl.[CH3:10][NH:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([S:27](=[O:30])(=[O:29])[NH2:28])[C:19]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][OH:16]>CC(C)=O>[CH3:10][NH:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([S:27](=[O:30])(=[O:29])[NH2:28])[C:19]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6344DichloromethaneHCID 541377545-(Hydroxymethyl)-3-(methylamino)-2-phenoxybenzene-1-sulfonamide

Product 1

HCID 202946325-Formyl-3-(methylamino)-2-phenoxybenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of dry pyridine (15 ml) and dry methylene chloride (225 ml), chromic anhydride (9.0 g) is added in one portion, and the mixture is stirred for 15 minutes. A solution of 3-methylamino-4-phenoxy-5-sulfamylbenzyl alcohol (4.6 g; prepared as described in Example 5) in acetone (25 ml) is then added in one portion and the mixture is stirred for a further 15 minutes. The resulting inorganic precipitate is removed by filtration and the filtrate is evaporated in vacuo. The residue is extracted with diethyl ether (300 ml) and filtered to remove a small amount of insoluble material. The diethyl ether is removed in vacuo to yield crude 3-methylamino-4-phenoxy-5-sulfamylbenzaldehyde. After recrystallization from ethanol it is obtained with a melting point of 166°-167° C.

Workup

  1. additionis added in one portion
  2. stirringthe mixture is stirred for a further 15 minutes
  3. customThe resulting inorganic precipitate is removed by filtration
  4. customthe filtrate is evaporated in vacuo
  5. extractionThe residue is extracted with diethyl ether (300 ml)
  6. filtrationfiltered
  7. customto remove a small amount of insoluble material
  8. customThe diethyl ether is removed in vacuo

Sources & evidence

ORD record
ord-124b18f48a554e7fbdffd015d1262397
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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