Diisopropylethylamine → HCID 178516941, 화합물

HRID 1296792노트

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HRID 1296792 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][NH2:6].[S:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=S.CCN(C(C)C)C(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][NH:6][C:12]1[S:11][CH2:17][C:15](=[O:16])[N:14]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 1445393-Chloro-4-fluorobenzylamineHCID 1201546Rhodanine

생성물 1

HCID 178516941HCID 178516941, 화합물수율 64.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

To a suspension of 3-chloro-4-fluorobenzylamine (2.5 g, 15.66 mmol) and Rhodanine (2 g, 15 mmol) in acetonitrile (50 mL) was added DIPEA (5.57 mL, 32 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (4.34 g, 16 mmol) was added in two portions within a period of 10 min. After addition, the suspension was allowed to warm to room temperature and stirred for 2 days. The resulting black solids were filtered through a plug of celite and washed with dichloromethane (200 mL) and methanol (500 mL). The combined solvents were removed under the vacuum and the crude residue was diluted with water (150 mL) and ethyl acetate (150 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the partial solvent under the vacuum gave lot of solids. After cooling in the refrigerator, the solids were collected by filtration and washed with cold ethyl acetate. After drying in air, 2.5 g (64% yield) of 2-(3-chloro-4-fluorobenzylamino)-thiazol-4-one was isolated as a white amorphous solid: EI-HRMS m/e calcd for C10H8ClFN2OS (M+) 258.0030. found 258.0029.

후처리

  1. additionAfter addition
  2. temperatureto warm to room temperature
  3. filtrationThe resulting black solids were filtered through a plug of celite
  4. washwashed with dichloromethane (200 mL) and methanol (500 mL)
  5. customThe combined solvents were removed under the vacuum
  6. additionthe crude residue was diluted with water (150 mL) and ethyl acetate (150 mL)
  7. customThe two layers were separated
  8. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  9. washThe combined organic extracts were washed with brine solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationFiltration of the drying agent and removal of the partial solvent under the vacuum
  12. customgave lot of solids
  13. temperatureAfter cooling in the refrigerator
  14. filtrationthe solids were collected by filtration
  15. washwashed with cold ethyl acetate
  16. customAfter drying in air

출처 및 근거

ORD 기록
ord-3edda0d480bd40e1bd18f2a53eb9c1e0
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07247727B2

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