1-Butanol → 2,1,3-Benzothiadiazole

HRID 1057088

반응식

HRID 1057088 반응식
Br[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5](Br)=[CH:4][CH:3]=1.C1(N(C2C=CC(B(O)O)=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)CCC>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N:7]1[S:8][N:9]=[C:10]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=12

참가 물질

8

반응물 4

HCID 2631-ButanolHCID 10340Sodium CarbonateHCID 6263614,7-Dibromo-2,1,3-benzothiadiazoleHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)

생성물 1

HCID 675022,1,3-Benzothiadiazole

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4,7-dibromobenzo[2,1,3]thiadiazole (13.2 g, 45 mmol), 4-(N,N-diphenylamino)phenylboronic acid (30.0 g, 104 mmol), a solution of sodium carbonate (21.2 g, 200 mmol) in water (80 mL), tetrakis(triphenylphosphine)palladium(0) (5.0 g, 4.3 mmol), n-butanol (800 mL), and toluene (400 mL) was stirred under argon and heated at 100° C. for 20 hours. After cooling to room temperature, the mixture was diluted with water (600 mL) and stirred for 2 hours. Finally, the reaction mixture was extracted with toluene (2 L), and the volatiles were removed under reduced pressure. The residue was chromatographed using silica gel and hexane/dichloromethane (1:1) as an eluent to give 26.96 g (43.3 mmol, 96%) of 4,7-bis[(N,N-diphenylamino)phenyl)]benzo[2,1,3]thiadiazole (Intermediate A).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionFinally, the reaction mixture was extracted with toluene (2 L)
  3. customthe volatiles were removed under reduced pressure
  4. customThe residue was chromatographed

출처 및 근거

ORD 기록
ord-4ea184599ce442c68f305d5075c1b48c
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399730B2

연결된 노트

불러오는 중…