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Hydrochloric Acid → C,C,C-Trifluoro-N-{3-[6-(5-fluorobenzothiazol-2-ylmethoxy)-2-methyl-4-oxo-4H-chromen-3-ylmethyl]phenyl}methanesulfonamide

HRID 1684632
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HRID 1684632 반응식
[F:1][C:2]([F:28])([F:27])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([OH:25])[CH:21]=3)[O:16][C:15]=2[CH3:26])[CH:8]=1)(=[O:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:36][C:37]1[S:38][C:39]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:40]=2[N:41]=1.Cl>CN(C)C=O.CCOCC.O>[F:28][C:2]([F:27])([F:1])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:36][C:37]4[S:38][C:39]5[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:40]=5[N:41]=4)[CH:21]=3)[O:16][C:15]=2[CH3:26])[CH:8]=1)(=[O:4])=[O:5]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 142042102-(Chloromethyl)-5-fluoro-1,3-benzothiazoleHCID 19039977C,C,C-Trifluoro-N-[3-(6-hydroxy-2-methyl-4-oxo-4H-chromen-3-yl-methyl)phenyl]methanesulfonamide

생성물 1

HCID 19039946C,C,C-Trifluoro-N-{3-[6-(5-fluorobenzothiazol-2-ylmethoxy)-2-methyl-4-oxo-4H-chromen-3-ylmethyl]phenyl}methanesulfonamide
수율 97%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 1.8 g (4.4 mmole) of the product from Example 126 in 50 mL dimethylformamide was added 2.4 g (17.4 mmole) potassium carbonate. The mixture was stirred at room temperature for 1 hour then 1.2 g (5.72 mmole) 2-(chloromethyl)-5-fluorobenzothiazole was added. The mixture was stirred for 18 hours, poured into water, acidified to ph 1-4 with 1N HCl, and extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine and then dried (MgSO4), and concentrated to give a solid. Trituration with ether afforded 2.45 g (97%) of the title product as a solid, mp 218°-220° C. Analysis calculated for C26H18N2S2O5F4 : C, 53.98; H, 3.14; N, 4.84. Found: C, 53.94; H, 2.91; N, 4.55.

후처리

  1. stirringThe mixture was stirred for 18 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give a solid

출처 및 근거

ORD 기록
ord-3a4997e7629540cea9d569b0cdd3e421
출처 데이터셋
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05641789

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