Methane → HCID 21845559, compound

HRID 619070Notes

Reaction equation

HRID 619070 reaction equation
Br.[C:2]1([C:12]2[N:13]=[C:14]([NH2:17])[S:15][CH:16]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([S:28](Cl)(=[O:30])=[O:29])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27].Cl.C>C(O)C.[OH-].[Na+].N1C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([S:28]([NH:17][C:14]2[S:15][CH:16]=[C:12]([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=[CH:4][CH:3]=3)[N:13]=2)(=[O:29])=[O:30])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

Participants

8

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 21845604HCID 21845604, compound

Product 1

HCID 21845559HCID 21845559, compoundYield 82.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1049PyridineSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 10 g of 4-(1-naphthyl)-thiazol-2-ylamine hydrobromide with 8.5 g of 3,4-dimethoxy-benzenesulfonyl chloride was stirred for 18 hours with 30 ml of pyridine. The resulting, red colored suspension was poured into 400 ml of 1N hydrochloric acid. The separated solid was dissolved in a mixture of 400 ml of ethanol and 400 ml of 2N sodium hydroxide solution. After the addition of 8 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. After neutralization with concentrated hydrochloric acid the mixture was concentrated and the residue was taken up with ethyl acetate, dried with magnesium sulphate and concentrated. Crystallization from 200 ml of ethyl acetate yielded 11.5 g of 3,4-dimethoxy-N-(4-naphthalen-1-yl-thiazol-2-yl)-benzenesulfonamide as colorless crystals.

Workup

  1. filtrationsubsequently the active charcoal was filtered off
  2. concentrationAfter neutralization with concentrated hydrochloric acid the mixture was concentrated
  3. dry with materialdried with magnesium sulphate
  4. concentrationconcentrated
  5. customCrystallization from 200 ml of ethyl acetate

Sources & evidence

ORD record
ord-81c5f60fc582486b8d9fc9ae5f4648bf
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Reaction notes

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