Dimethylamine → 3,4-Dimethoxy-N-[4-(3-nitrophenyl)-5-dimethylaminomethyl-1,3-thiazole-2-yl]benzenesulfonamide

HRID 1671666

Reaction equation

HRID 1671666 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([NH:14][C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=3)[N:19]=2)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:29]=O.[CH3:31][NH:32][CH3:33].O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([NH:14][C:15]2[S:16][C:17]([CH2:31][N:32]([CH3:29])[CH3:33])=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=3)[N:19]=2)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 962WaterHCID 52823373,4-Dimethoxy-N-(4-(3-nitrophenyl)-2-thiazolyl)benzenesulfonamide

Product 1

HCID 248121243,4-Dimethoxy-N-[4-(3-nitrophenyl)-5-dimethylaminomethyl-1,3-thiazole-2-yl]benzenesulfonamideYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3,4-dimethoxy-N-(4-(3-nitrophenyl)thiazol-2-yl)benzenesulfonamide (0.267 g, 0.68 mmol) in ethanol (10 mL, warming required) was added an aqueous solution of formaldehyde (37%, 0.5 mL, about 0.194 g, 6.5 mmol) followed by the dropwise addition of a solution of dimethylamine in water (60 wt %, 55 mL, about 0.274 g, 6.1 mmol). The addition was slightly exothermic, and the pale yellow solution became yellow-orange in color. After 0.5 h, a pale yellow solid separated from solution. After 19 h, the solid was collected by filtration, it was washed with ethanol, and dried in vacuo to give a pale yellow solid (0.277 g, 86.3% yield), mp 203° C.

Workup

  1. additionThe addition
  2. customa pale yellow solid separated from solution
  3. waitAfter 19 h
  4. filtrationthe solid was collected by filtration, it
  5. washwas washed with ethanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b76905cfb3204e5985abab8a11309238
Source dataset
uspto-grants-2011_08
Patent number
US07994338B2

Linked notes

Loading…