Diisopropylethylamine → HCID 12004111, 화합물

HRID 908657노트

반응식

HRID 908657 반응식
[Cl:1][C:2]([Cl:19])=[CH:3][CH2:4][O:5][C:6]1[CH:16]=[C:15]([Cl:17])[C:9]([O:10][CH2:11][C:12]([OH:14])=O)=[C:8]([Cl:18])[CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:53][C:54]([F:66])([F:65])[C:55]1[CH:56]=[C:57]([CH:62]=[CH:63][CH:64]=1)[C:58](=[N:60]O)[NH2:59]>CN(C=O)C.O.C1C=CC2N(O)N=NC=2C=1>[Cl:19][C:2]([Cl:1])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([Cl:18])[C:9]([O:10][CH2:11][C:12]2[O:14][N:60]=[C:58]([C:57]3[CH:62]=[CH:63][CH:64]=[C:55]([C:54]([F:53])([F:65])[F:66])[CH:56]=3)[N:59]=2)=[C:15]([Cl:17])[CH:16]=1

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 609330N'-hydroxy-3-(trifluoromethyl)benzimidamideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59366526HCID 59366526, 화합물

생성물 1

HCID 12004111HCID 12004111, 화합물수율 184%

시약·촉매·용매 3

HCID 757711-Hydroxybenzotriazole촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 0.129 gram (0.00037 mole) of 2-(4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy)acetic acid in 1.9 mL of DMF was added 0.141 gram (0.00037 mole) of HBTU, 0.008 gram (0.00006 mole) of HOBT and 0.24 gram (0.0019 mole) of DIEA. The reaction mixture stirred for 10 minutes at which time 0.075 gram (0.00037 mole) of 3-(trifluoromethyl)benzamidoxime was added. Upon completion of addition the reaction mixture was stirred at ambient temperature then heated to 112° C. where it stirred for four hours. After this time the reaction mixture was cooled to ambient temperature, diluted with water and extracted with a mixture of hexanes and ethyl acetate (70:30). The extract was washed in succession with two 5 mL portions of water, one 5 mL portion of an aqueous hydrochloric acid solution and one 5 mL portion of aqueous sodium bicarbonate, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using a mixture of hexanes and ethyl acetate as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.35 gram of the subject compound as an off-white solid.

후처리

  1. additionwas added
  2. additionUpon completion of addition the reaction mixture
  3. temperaturethen heated to 112° C. where it
  4. stirringstirred for four hours
  5. temperatureAfter this time the reaction mixture was cooled to ambient temperature
  6. extractionextracted with a mixture of hexanes and ethyl acetate (70:30)
  7. washThe extract was washed in succession with two 5 mL portions of water, one 5 mL portion of an aqueous hydrochloric acid solution and one 5 mL portion of aqueous sodium bicarbonate
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure to a residue
  11. customThe residue was purified with column chromatography on silica gel using
  12. additiona mixture of hexanes and ethyl acetate as an eluant
  13. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c5680c76d642470292de299032d0b987
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017635B2

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