N,N-Dimethylaniline → HCID 86603515, 화합물

HRID 2214333

반응식

HRID 2214333 반응식
[C:1]1([O:7][C:8]([C:10]2[CH:18]=[CH:17][C:13]3[NH:14][N:15]=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19](Cl)=[O:20].[CH2:22]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:36]=1[NH:42][C:43]([C:45]1[CH:46]=[C:47]([O:56][C:57](=[O:66])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[NH:64][CH3:65])[C:48]2[C:53]([C:54]=1[OH:55])=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:44])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].CN(C)C1C=CC=CC=1>C1COCC1.C(#N)C>[CH2:22]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:36]=1[NH:42][C:43]([C:45]1[CH:46]=[C:47]([O:56][C:57]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[N:64]([CH3:65])[C:19]([N:14]2[C:13]3[CH:17]=[CH:18][C:10]([C:8]([O:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[O:9])=[CH:11][C:12]=3[N:16]=[N:15]2)=[O:20])=[O:66])[C:48]2[C:53]([C:54]=1[OH:55])=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:44])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

참가 물질

7

반응물 4

HCID 949N,N-DimethylanilineHCID 75720Formyl chlorideHCID 69589732HCID 69589732, 화합물HCID 178524280HCID 178524280, 화합물

생성물 1

HCID 86603515HCID 86603515, 화합물

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매2회

실험 절차

1H-Benzotriazole-5-carboxylic acid phenyl ester, compound with formyl chloride(15.4 g, 0.051 mol) was dissolved in THF (200 ml) and added dropwise during 20 min to a solution of 2-methylamino-benzoic acid 3-(2-dodecyloxy-5-methyl-phenylcarbamoyl)-4-hydroxy-naphthalen-1-yl ester (31.1 g, 0.051 mol) and N,N-dimethylaniline (11.8 g, 0.097 mol) in THF (120 ml). The solution was stirred overnight. Liquid chromatography coupled to mass spectrometry indicated that the major product was the desired coupler, present as a mixture of two isomers. The solvent was removed by evaporation under reduced pressure and the crude oil re-dissolved in ethyl acetate (900 ml). The solution was washed with aqueous 2 M hydrochloric acid (500 ml) and then water (500 ml) in a separating funnel, separated, dried over anhydrous magnesium sulfate, filtered and re-evaporated to give a brownish gum. The residue was re-dissolved by warming in acetonitrile (500 ml), using a steam bath. This solution was then stirred for 60 hr at room temperature. A beige solid formed which was filtered and dried under vacuo. Analysis was consistent with the desired product as a mixture of 1H and 3H triazole isomers. The total yield of product was 39.6 g (88%).

후처리

  1. additionpresent as a mixture of two isomers
  2. customThe solvent was removed by evaporation under reduced pressure
  3. dissolutionthe crude oil re-dissolved in ethyl acetate (900 ml)
  4. washThe solution was washed with aqueous 2 M hydrochloric acid (500 ml)
  5. customwater (500 ml) in a separating funnel, separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customre-evaporated
  9. customto give a brownish gum
  10. dissolutionThe residue was re-dissolved
  11. stirringThis solution was then stirred for 60 hr at room temperature
  12. customA beige solid formed which
  13. filtrationwas filtered
  14. customdried under vacuo
  15. additionAnalysis was consistent with the desired product as a mixture of 1H and 3H triazole isomers

출처 및 근거

ORD 기록
ord-90c315f64b1b466dba1790801816e545
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07108964B2

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