Pyridine → 5-Formyl-3-(methylamino)-2-phenoxybenzene-1-sulfonamide
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
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 (4.6g; prepared as described in Example 5) in acetone (25 ml) is then added in one portion and the mixture is stired 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
- additionis added in one portion
- waitthe mixture is stired for a further 15 minutes
- customThe resulting inorganic precipitate is removed by filtration
- customthe filtrate is evaporated in vacuo
- extractionThe residue is extracted with diethyl ether (300 ml)
- filtrationfiltered
- customto remove a small amount of insoluble material
- customThe diethyl ether is removed in vacuo
Sources & evidence
- ORD record
- ord-83b17e5f3e5b4e04bc96747c35c99305
- Source dataset
- uspto-grants-1978_04
- Patent number
- US04082851
Reaction notes
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