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Hydrochloric Acid → 7-Chlorothieno[3,2-b]pyridine-2-carbothioamide

HRID 889891
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HRID 889891 반응식
COC[NH:4][C:5]([C:7]1[S:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[Cl:16])[CH:8]=1)=[S:6].Cl.[NH4+].[OH-]>C1COCC1>[Cl:16][C:13]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:8]=[C:7]([C:5](=[S:6])[NH2:4])[S:15][C:14]=12
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 858021057-Chloro-thieno[3,2-b]pyridine-2-carbothioic acid methoxymethyl amide

생성물 1

HCID 235951097-Chlorothieno[3,2-b]pyridine-2-carbothioamide수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 7-Chloro-thieno[3,2-b]pyridine-2-carbothioic acid methoxymethyl-amide (93.9 g, 344 mmol) and 900 mL THF was added 1 N HCl (344 mL, 344 mmol). The reaction mixture was heated to reflux for seventy-two hours. The reaction mixture was cooled to 0° C., and 300 mL of concentrated NH4OH was added and stirred. The THF was removed under reduced pressure and the residue was suspended in ethyl acetate and stirred. The precipitate was filtered, washed with ethyl acetate and dried to give 7-chloro-thieno[3,2-b]pyridine-2-carbothioic acid amide (66.7 g) in 85% yield. C8H5ClN2S2: APCI m/z: 228.9/230.9 (MH+); 1H NMR (d6-DMSO): δ 10.24 (s, 1H), 9.94 (s, 1H), 8.65 (d, 1H, J=5.0 Hz), 8.19 (s, 1H), 7.62 (d, 1H, J=5.0 Hz) ppm.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for seventy-two hours
  3. customThe THF was removed under reduced pressure
  4. stirringstirred
  5. filtrationThe precipitate was filtered
  6. washwashed with ethyl acetate
  7. customdried

출처 및 근거

ORD 기록
ord-09de6772c24f47988860595e7be7a232
출처 데이터셋
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06995171B2

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