Methyl iodide → 5-(Hydroxymethyl)-3-(methylamino)-2-phenoxybenzene-1-sulfonamide

HRID 1390051Notes

Reaction equation

HRID 1390051 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([S:17](=[O:20])(=[O:19])[NH2:18])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][OH:6].CI.[C:23](=O)([O-])O.[Na+].CN(C)P(=O)(N(C)C)N(C)C>O>[CH3:23][NH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([S:17](=[O:20])(=[O:19])[NH2:18])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][OH:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 516892Sodium BicarbonateHCID 540361913-Amino-5-(hydroxymethyl)-2-phenoxybenzene-1-sulfonamide

Product 1

HCID 541377545-(Hydroxymethyl)-3-(methylamino)-2-phenoxybenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-amino-4-phenoxy-5-sulfamylbenzyl alcohol (8.8 g; prepared as described in Example 2), methyl iodide (2.1 ml), sodium hydrogen carbonate (5.0 g) and hexamethylphosphoric triamide (45 ml) is stirred at 22°-25° C. for 18 hours. The mixture is then diluted with water (about 500 ml) to precipitate crude 3-methylamino-4-phenoxy-5-sulfamylbenzyl alcohol. After recrystallization from aqueous ethanol it is obtained with a melting point of 167°-168° C.

Workup

  1. customto precipitate crude 3-methylamino-4-phenoxy-5-sulfamylbenzyl alcohol
  2. customAfter recrystallization from aqueous ethanol it
  3. customis obtained with a melting point of 167°-168° C.

Sources & evidence

ORD record
ord-9add2441c273498b839e5427928bcbf6
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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