2-Amino-4-chlorophenol → 2-Amino-4-chlorophenyl methanesulfonate

HRID 1647659Notes

Reaction equation

HRID 1647659 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[OH:14].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:14][C:8]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=1[NH2:6])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 72652-Amino-4-chlorophenolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 199209072-Amino-4-chlorophenyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

174.5 g (1.52 mol) of methanesulfonyl chloride were added dropwise at 10°-15° C. to a solution of 218.7 g (1.52 mol) of 2-amino-4-chlorophenol and 153.8 g (1.52 mol) of triethylamine in 400 ml of methylene chloride. The mixture was stirred for 18 hours at 25° C. and was introduced into ice water, and the organic phase was separated off, washed twice with water and dried over Na2SO4. After the solvent had been distilled off, a gradually crystallizing residue of the product remained, which was sufficiently pure for further reaction (329.5 g, 98% of theory). The product could be recrystallized from methanol/water (mp. 70°-71° C.).

Workup

  1. customthe organic phase was separated off
  2. washwashed twice with water
  3. dry with materialdried over Na2SO4
  4. distillationAfter the solvent had been distilled off
  5. customwhich was sufficiently pure for further reaction (329.5 g, 98% of theory)
  6. customThe product could be recrystallized from methanol/water (mp. 70°-71° C.)

Sources & evidence

ORD record
ord-106fd56240a047d7814244d2dbbf0d57
Source dataset
uspto-grants-1995_07
Patent number
US05434124

Reaction notes

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