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Sodium Carbonate → 6,7-Difluorobenzo[B]thiazolo[3,4-D][1,4]oxazine-1(4H)-thione

HRID 1382737
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HRID 1382737 반응식
[OH:1][CH2:2][C:3]1[N:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[C:10]=2F)[C:5](=[S:8])[S:6][CH:7]=1.[H-].[Na+].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C(#N)C.CN(C)C=O>[F:16][C:11]1[C:10]2[O:1][CH2:2][C:3]3=[CH:7][S:6][C:5](=[S:8])[N:4]3[C:9]=2[CH:14]=[CH:13][C:12]=1[F:15]
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참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 146733094-hydroxymethyl-3-(2,3,4-trifluorophenyl)-2(3H)-thiazolethione

생성물 1

HCID 146733106,7-Difluorobenzo[B]thiazolo[3,4-D][1,4]oxazine-1(4H)-thione

시약·촉매·용매 3

HCID 6228
Dimethylformamide
용매
HCID 6342Acetonitrile용매
HCID 312751,4-Dioxane용매

실험 절차

That is, first the compound (VI) is obtained from the compound (V) in the same manner as in the process (a). The compound (VI) is then reacted with 1-acetoxy-3-halogenoacetone in an organic solvent such as chloroform, methylene chloride or a lower alcohol to give 3-acetoxy-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamate (XVI). The compound (XVI) is then heated with an inorganic acid such as hydrochloric acid or sulfuric acid in a lower alcohol such as ethanol to give 4-hydroxymethyl-3-(2,3,4-trifluorophenyl)-2(3H)-1,3-thiazolethione (XVII). The compound (XVII) is then reacted with an inorganic base such as sodium hydride, potassium carbonate or sodium carbonate in an aprotic organic solvent such as N,N-dimethylformamide, acetonitrile or dioxane to give 6,7-difluoro-1H,4H-thiazolo[4,3-c][1,4]benzoxazine-1-thione (XVIII). The compound (XVIII) is then reacted with a lower alkyl halide such as methyl iodide or ethyl iodide in a polar organic solvent such as N,N-dimethylformamide, acetonitrile or ethanol to give 6,7-difluoro-1-alkylthio-4H-[1,4]benzoxazino[4,3-c]thiazolium halide (XIX). The compound (XIX) is then reacted with di(lower alkyl) malonate sodium salt, which is prepared from di(lower alkyl) malonate and sodium hydride, in an organic solvent such as tetrahydrofuran or dioxane to give di(lower alkyl) (6,7-difluoro-1H,4H-thiazolo[4,3-c][1,4]benzoxazin-1-ylidene)malonate (XI), which is treated in the same manner as in the process (a) to give the compound (II).

출처 및 근거

ORD 기록
ord-19c1a99ed3254571a5b94bd9e3203c42
출처 데이터셋
uspto-grants-1989_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04808584

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