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Oxalyl chloride → N-(4-Chloro-3-methyl-5-isothiazolyl)-2-(2,2-dimethylpropyl)-5-benzoxazoleacetamide

HRID 48151
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HRID 48151 반응식
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][C:7]=2[N:8]=1.C(Cl)(=O)C(Cl)=O.[NH2:25][C:26]1[S:30][N:29]=[C:28]([CH3:31])[C:27]=1[Cl:32]>ClCCl.CN(C)C=O.C(OCC)(=O)C>[Cl:32][C:27]1[C:28]([CH3:31])=[N:29][S:30][C:26]=1[NH:25][C:14](=[O:16])[CH2:13][C:10]1[CH:11]=[CH:12][C:6]2[O:5][C:4]([CH2:3][C:2]([CH3:1])([CH3:18])[CH3:17])=[N:8][C:7]=2[CH:9]=1
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참가 물질

7

반응물 3

HCID 65578Oxalyl chlorideHCID 112405714-Chloro-3-methyl-1,2-thiazol-5-amineHCID 22742085[2-(2,2-Dimethylpropyl)-1,3-benzoxazol-5-yl]acetic acid

생성물 1

HCID 22742093N-(4-Chloro-3-methyl-5-isothiazolyl)-2-(2,2-dimethylpropyl)-5-benzoxazoleacetamide수율 28.7%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매
HCID 6344
Dichloromethane
용매
HCID 8857Ethyl Acetate용매

실험 절차

[2-(2,2-Dimethylpropyl)benzoxazol-5-yl]acetic acid [from step 7] (0.800 g, 0.003 mole) was suspended in dichloromethane (10 ml) and N,N-dimethylformamide (one drop) and oxalyl chloride (0.451 g, 0.004 mole) were added sequentially. The mixture was stirred for 2 hour and then the solvent was removed in vacuo. The residue was taken up in xylene (10 ml), 5-amino-4-chloro-3-methylisothiazole [from step 1] (0.829 g, 0.006 mole) was added and then the mixture was heated under reflux for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with brine. The organic solution was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was further purified by flash column chromatography on silica gel, eluting with a 2:1 mixture of hexane:ethyl acetate, to give N-(4-chloro-3-methylisothiazol-5-yl)-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide (0.325 g) as a pale orange solid, m.p. 144-145° C.

후처리

  1. customthe solvent was removed in vacuo
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. washwashed with brine
  5. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo
  8. customThe residue was further purified by flash column chromatography on silica gel
  9. washeluting with a 2:1 mixture of hexane

출처 및 근거

ORD 기록
ord-990a42d2922f47be86b39cda0187f00b
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06703347B2

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