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

HRID 1722079
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HRID 1722079 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.C(=O)([O-])[O-].[K+].[K+]>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

4

반응물 2

HCID 11430Potassium CarbonateHCID 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)-thione수율 91.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
110 °C

실험 절차

4-Hydroxymethyl-3-(2,3,4-trifluorophenyl)-2(3H)-thiazolethione (60 g) prepared in the same manner as in Reference Example 19 was dissolved in N,N-dimethylformamide (450 ml) and thereto potassium carbonate (60 g) was added and the mixture was stirred at 110° C. for 3 hours. After the reaction mixture was evaporated to dryness, water was added to the residue and the resultant was extracted with chloroform. The extract was washed with a NaCl solution and dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. The residue was recrystallized from a mixed solvent of hexane-ethyl acetate to give the title compound (51 g) as pale yellow crystals, m.p. 163°-167° C.

후처리

  1. customAfter the reaction mixture was evaporated to dryness, water
  2. additionwas added to the residue
  3. extractionthe resultant was extracted with chloroform
  4. washThe extract was washed with a NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe residue was recrystallized from a mixed solvent of hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-7d9bad2b75514244a5586a0d16e8d691
출처 데이터셋
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04853469

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