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

HRID 1287835Notes

Reaction equation

HRID 1287835 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-a8e8739c00a64195ad27339a80e4241a
Source dataset
uspto-grants-1976_10
Patent number
US03985885

Reaction notes

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