Methylamine → 4-Amino-2-chloro-5-[(methylamino)sulfonyl]benzenesulfonyl chloride

HRID 979772Notes

Reaction equation

HRID 979772 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([Cl:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[S:13](Cl)(=[O:15])=[O:14].CN.[CH2:19]([N:21](CC)CC)C>O1CCCC1.C1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([Cl:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[S:13]([NH:21][CH3:19])(=[O:15])=[O:14]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 695934-Amino-6-chlorobenzene-1,3-di(sulphonyl chloride)

Product 1

HCID 137554674-Amino-2-chloro-5-[(methylamino)sulfonyl]benzenesulfonyl chloride

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cool a solution of 4-amino-6-chloro-1,3-benzenedisulfonyl chloride (32.3 g) in tetrahydrofuran (THF, 150 ml) to -78° C. under a nitrogen atmosphere. Add a solution of 1.45 Molar methylamine in benzene (100 ml) containing triethylamine (10.1 g) dropwise with stirring over 45 minutes. After the addition is complete, stir at room temperature for 3 hours. Vacuum evaporate the solvent and partition the residue between ethyl acetate (EtOAc) (500 ml) and 10% aqueous citric acid (50 ml). Separate the organic layer and wash with saturated aqueous NaHCO3 (100 ml) followed by brine (100 ml). Dry the solution over Na2SO4, filter and vacuum evaporate the solvent. Triturate the residue with ether (100 ml) and collect the product by filtration. Vacuum dry at room temperature to give the title compound, m.p. 153°-155° C. Rf (silica gel; CH2Cl2 :EtOAc,97:3)=0.40.

Workup

  1. additionAfter the addition
  2. stirringstir at room temperature for 3 hours
  3. customVacuum evaporate the solvent
  4. custompartition the residue between ethyl acetate (EtOAc) (500 ml) and 10% aqueous citric acid (50 ml)
  5. customSeparate the organic layer
  6. washwash with saturated aqueous NaHCO3 (100 ml)
  7. dry with materialDry the solution over Na2SO4
  8. filtrationfilter
  9. customvacuum evaporate the solvent
  10. customTriturate the residue with ether (100 ml)
  11. customcollect the product
  12. filtrationby filtration
  13. customVacuum dry at room temperature

Sources & evidence

ORD record
ord-135462b480d2424b8a833ed8ee27c2ef
Source dataset
uspto-grants-1987_01
Patent number
US04634689

Reaction notes

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