Chlorosuccinimide → 4-Chloro-2-(pyridin-3-yl)-1,3-thiazol-5-amine hydrochloride

HRID 882000노트

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HRID 882000 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([NH2:12])=[CH:10][N:11]=2)[CH:2]=1.[Cl:13]N1C(=O)CCC1=O>O1CCOCC1>[ClH:13].[Cl:13][C:10]1[N:11]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[S:8][C:9]=1[NH2:12]

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 457887112-(3-Pyridinyl)-1,3-thiazol-5-amine

생성물 1

HCID 867043434-Chloro-2-(pyridin-3-yl)-1,3-thiazol-5-amine hydrochloride수율 170.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
0 °C

실험 절차

To a dry 250 ml round bottom flask equipped with magnetic stirrer, was charged 6.3 g (35.5 mmoles) of 2-(pyridin-3-yl)-1,3-thiazol-5-amine, and 100 mLs of anhydrous 1,4-dioxane. The solution was cooled to ˜0° C. and 4.75 g (35.5 mmoles) of N-chlorosuccinimide was added portionwise at a rate that maintained the temperature below 10° C. The reaction mixture was stirred at 5-10° C. for 20 minutes, and then filtered through a small pad of diatomaceous earth. The filtrate was diluted with 50 mLs of diethyl ether, and acidified with 10 mLs of 4.0 M HCl in 1,4-dioxane. The resulting solid was collected by vacuum filtration, washed with ethyl ether (100 mLs) and methylene chloride (500 mLs), and then dried in vacuuo at 40° C. to afford 7.5 g (85%) of an orange solid: 1H NMR (400 MHz, DMSO-d6) δ 9.08 (d, J=2.1 Hz, 1H), 8.76 (dt, J=9.5, 4.7 Hz, 1H), 8.66 (ddd, J=8.3, 2.0, 1.3 Hz, 1H), 7.97 (dt, J=15.6, 7.8 Hz, 1H).

후처리

  1. customTo a dry 250 ml round bottom flask equipped with magnetic stirrer
  2. temperaturemaintained the temperature below 10° C
  3. filtrationfiltered through a small pad of diatomaceous earth
  4. additionThe filtrate was diluted with 50 mLs of diethyl ether
  5. filtrationThe resulting solid was collected by vacuum filtration
  6. washwashed with ethyl ether (100 mLs) and methylene chloride (500 mLs)
  7. customdried in vacuuo at 40° C.

출처 및 근거

ORD 기록
ord-31f5f11fc0d344239de924f386f8d688
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993769B2

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