Tetrahydrofuran → 5-Isothiocyanato-6-methoxy-2-(pyridin-3-yl)-1,3-benzothiazole

HRID 1287835노트

반응식

HRID 1287835 반응식
[NH2:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=CN=3)=[N:7][C:6]=2[CH:16]=1.O1CCCC1.[C:24](Cl)(Cl)=[S:25].[CH2:28]([N:30](CC)CC)C>>[N:1]([C:2]1[C:3]([O:17][CH3:18])=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:28]=[N:30][CH:13]=[CH:14][CH:15]=3)=[N:7][C:6]=2[CH:16]=1)=[C:24]=[S:25]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 215066906-Methoxy-2-(pyridin-2-yl)-1,3-benzothiazol-5-amine

생성물 1

HCID 127819095-Isothiocyanato-6-methoxy-2-(pyridin-3-yl)-1,3-benzothiazole

실험 절차

5-Amino-6-methoxy-2-(2-pyridinyl)benzothiazole, 8.3 g, 0.0325 mole, is dissolved in 400 cc of tetrahydrofuran containing 9.5 cc, 0.065 mole of triethylamine. Thiophosgene, 2.5 cc, 0.0325 mole, is added, and the resulting mixture stirred at ambient temperature for 4 hours. The precipitate which forms is filtered and washed with tetrahydrofuran. The filtrate is concentrated to dryness. The residue is adsorbed on a silica gel column and eluted with hexane-ethylacetate to yield 1.8 g of crude product. Recrystallization from MeCN/CHCl3 yields 1.2 g of the title product, m.p. 164°-166°.

후처리

  1. filtrationThe precipitate which forms is filtered
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate is concentrated to dryness
  4. washeluted with hexane-ethylacetate
  5. customto yield 1.8 g of crude product
  6. customRecrystallization from MeCN/CHCl3

출처 및 근거

ORD 기록
ord-a8e8739c00a64195ad27339a80e4241a
출처 데이터셋
uspto-grants-1976_10
특허 번호
US03985885

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