Sodium Sulfite → HCID 19065141, compound

HRID 265336Notes

Reaction equation

HRID 265336 reaction equation
[CH2:1]([C:3]1[S:4][C:5]2[N:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:20])C=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH2:1]([C:3]1[S:4][C:5]2[N+:11]([O-:20])=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acid2×HCID 19065152HCID 19065152, compound

Product 1

HCID 19065141HCID 19065141, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Ethyl-7-azabenzothiazole (2.95 g) was dissolved in dichloromethane (30 ml), and meta-chloroperbenzoic acid (4.7 g) was added to the solution at room temperature. After 3.5 hours, meta-chloroperbenzoic acid (2.3 g). was further added. After completion of a reaction, the reaction mixture was treated with an aqueous solution of sodium sulfite while chilling with ice water. The thus-treated reaction mixture was diluted with dichloromethane, and the resultant organic layer was washed with aqueous sodium hydrogencarbonate, water and saline in that order, and dried. The solvent was distilled out to obtain 2-ethyl-7-azabenzothiazole-7-oxide (2.69 g). This compound was added to dichloromethane (27 ml), and dimethylaminocarbamoyl chloride (4.16 g), trimethylsilyl cyanide (5.69 ml) and triethylamine (6.3 ml) were successively added to conduct a reaction for 8 hours at room temperature. Trimethylsilyl cyanide (2.5 ml) and dimethylaminocarbamoyl chloride (2.5 ml) were further added. After the reaction was conducted for 2 days at room temperature, aqueous sodium hydrogencarbonate was added to the reaction mixture, followed by stirring for 1 hour. The reaction mixture was subjected to extraction with ethyl acetate, and the resultant organic layer was washed with water, dried and evaporated. After purifying the residue through a silica gel column (eluthion with dichloromethane: methanol=200:1), recrystallization from dichloromethaneisopropyl ether was conducted to form 2-ethyl=6-cyano-7-azabenzothiazole (1.37 g). The intended compound was obtained in accordance with the same procedure as that of Example 106 except that the above compound was used in place of 2-ethyl-6-chlorobenzothiazole. Physical properties of this compound are described below.

Workup

  1. additionwas further added
  2. customAfter completion of a reaction
  3. customThe thus-treated reaction mixture
  4. washthe resultant organic layer was washed with aqueous sodium hydrogencarbonate, water and saline in that order
  5. customdried
  6. distillationThe solvent was distilled out

Sources & evidence

ORD record
ord-63f21184232b4953bac870b82e066073
Source dataset
uspto-grants-1997_07
Patent number
US05648372

Reaction notes

Loading…