Hydrochloric Acid → 1-(2-amino-3,4,5-trimethoxyphenyl)-2-(N-methylsulphamoyl)ethanone

HRID 622692Notes

Reaction equation

HRID 622692 reaction equation
[CH3:1][NH:2][S:3]([CH3:6])(=[O:5])=[O:4].C([Li])CCC.[NH2:12][C:13]1[C:22]([O:23][CH3:24])=[C:21]([O:25][CH3:26])[C:20]([O:27][CH3:28])=[CH:19][C:14]=1[C:15](OC)=[O:16].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1.CCCCCC>[NH2:12][C:13]1[C:22]([O:23][CH3:24])=[C:21]([O:25][CH3:26])[C:20]([O:27][CH3:28])=[CH:19][C:14]=1[C:15](=[O:16])[CH2:6][S:3](=[O:5])(=[O:4])[NH:2][CH3:1]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 78735Methyl 3,4,5-trimethoxyanthranilateHCID 97632N-MethylmethanesulfonamideHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 212914851-(2-amino-3,4,5-trimethoxyphenyl)-2-(N-methylsulphamoyl)ethanone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred solution of N-methylmethanesulphonamide (13.6 g) in dry tetrahydrofuran (160 ml) at -70° to -60° was added a solution of n-butyl lithium in hexane (2.5M; 100 ml) under argon. The mixture was stirred at -78° for 1 hour and a solution of methyl 2-amino-3,4,5-trimethoxybenzoate (10 g) in dry tetrahydrofuran (50 ml) was added at -70° to -60°. The mixture was stirred for 2 hours, during which time the temperature rose to 10°. The mixture was poured on to ice (500 g), acidified to pH 1 with 5N HCl, and then neutralised to pH 7 with saturated aqueous sodium bicarbonate. The solid product was extracted into dichloromethane (3×500 ml). The extract was dried and evaporated to give a residue. This residue was triturated with ether to give a solid which was collected, dried and crystallised from ethyl acetate to give the novel compound 1-(2-amino-3,4,5-trimethoxyphenyl)-2-(N-methylsulphamoyl)ethanone, m.p. 125°-127°.

Workup

  1. stirringThe mixture was stirred for 2 hours, during which time the temperature
  2. customrose to 10°
  3. extractionThe solid product was extracted into dichloromethane (3×500 ml)
  4. customThe extract was dried
  5. customevaporated
  6. customto give a residue
  7. customThis residue was triturated with ether
  8. customto give a solid which
  9. customwas collected
  10. customdried
  11. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-b1a89640f08641e8b6392c9eecfcc456
Source dataset
uspto-grants-1988_09
Patent number
US04772614

Reaction notes

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