Triethylamine → 5-Isothiocyanato-2-(pyridin-3-yl)-1,3-benzothiazole

HRID 1287832Notes

Reaction equation

HRID 1287832 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[N:7][C:6]=2[CH:16]=1.C(N(CC)CC)C.[C:24](Cl)(Cl)=[S:25]>O1CCCC1>[N:1]([C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[N:7][C:6]=2[CH:16]=1)=[C:24]=[S:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 215067025-Amino-2-(3-pyridinyl)benzothiazole

Product 1

HCID 127819065-Isothiocyanato-2-(pyridin-3-yl)-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-2-(3-pyridinyl)benzothiazole, 8.0 g, 0.035 M, is dissolved in 400 cc of tetrahydrofuran and 9.8 cc, 0.070 M, of triethylamine. Thiophosgene, 2.7 cc, 0.035 M is added, and the resulting mixture stirred overnight at ambient temperature. The solids which form are filtered and washed with tetrahydrofuran. The filtrate is concentrated to dryness and chromatographed on Alumina IV; elution with benzene yields 1.0 g of white solid which is recrystallized from acetonitrile to yield the title compound, 0.52 g, m.p. 160°-162° (12% of theory).

Workup

  1. filtrationThe solids which form are filtered
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate is concentrated to dryness
  4. customchromatographed on Alumina IV
  5. washelution with benzene

Sources & evidence

ORD record
ord-ee00167b7a774619a597eb9d0ab59a5e
Source dataset
uspto-grants-1976_10
Patent number
US03985885

Reaction notes

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