Sodium Chloride → 2,7-dichloro-4-methyl-1,3-benzothiazole

HRID 2427172노트

반응식

HRID 2427172 반응식
N[C:2]1[S:3][C:4]2[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([CH3:12])[C:5]=2[N:6]=1.N([O-])=O.[Na+].[Na+].[Cl-:18]>OP(O)(O)=O.O>[Cl:18][C:2]1[S:3][C:4]2[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([CH3:12])[C:5]=2[N:6]=1

참가 물질

6

반응물 3

HCID 5234Sodium ChlorideHCID 20498937-Chloro-4-methyl-1,3-benzothiazol-2-amineHCID 23668193Sodium Nitrite

생성물 1

HCID 20498762,7-dichloro-4-methyl-1,3-benzothiazole수율 64.1%

시약·촉매·용매 2

HCID 962Water용매2회HCID 1004Phosphoric Acid용매

실험 절차

To a slurry of 2-amino-4-methyl-7-chlorobenzothiazole (77.2) (6.37 g) in H3PO4 (85%, 213 ml) in a 500 ml 3-necked flask with mechanical stirring and an internal temperature of <−10° C., was added dropwise a solution of NaNO2 (6.87 g) in water (11 ml). The mixture was warmed to 0° for 30 minutes and then recooled. The slurry was then slowly added to a cold (˜5° C.) solution of CuSO4.5H2O (32 g) and NaCl (40 g) in water (128 ml) with vigorous mechanical stirring. After the foaming subsides and warming to RT, the solids were collected by filtration and rinsed with water. The solids were dissolved in ether leaving some insoluble residue. The ether solution was washed with water, and sodium bicarbonate solution. After the organic layer was concentrated, the residue was purified by flash chromatography with 10% methylene chloride in hexane to afford 2-chloro-4-methyl-7-chlorobenzothiazole (77.3) (4.48 g).

후처리

  1. temperatureThe mixture was warmed to 0° for 30 minutes
  2. filtrationthe solids were collected by filtration
  3. washrinsed with water
  4. dissolutionThe solids were dissolved in ether leaving some insoluble residue
  5. washThe ether solution was washed with water, and sodium bicarbonate solution
  6. concentrationAfter the organic layer was concentrated
  7. customthe residue was purified by flash chromatography with 10% methylene chloride in hexane

출처 및 근거

ORD 기록
ord-450af63169cf48888053897f4b5dbf52
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968567B2

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