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

HRID 1287837Notes

Reaction equation

HRID 1287837 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)=[N:7][C:6]=2[CH:15]=1.C(N(CC)CC)C.[C:23](Cl)(Cl)=[S:24]>O1CCCC1>[N:1]([C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)=[N:7][C:6]=2[CH:15]=1)=[C:23]=[S:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 215066992-(Thiophen-2-yl)-1,3-benzothiazol-5-amine

Product 1

HCID 127819415-Isothiocyanato-2-(thiophen-2-yl)-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-2-(2-thienyl)benzothiazole 7.0 g, 0.03 M is dissolved in 400 cc of tetrahydrofuran and 8.4 cc, 0.06 M, of triethylamine. Thiophosgene 2.3 cc, 0.03 M, is added, and the resulting mixture stirred at ambient temperature overnight. The solids which form are filtered, and washed with tetrahydrofuran. The filtrate is concentrated to dryness, and chromatographed on Alumina IV. The product is recrystallized from acetonitrile to yield 5.7 g of colorless needles, 70% of theory, m.p. 147°-149°.

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. customThe product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-67a8f48d06794da59e54157f6e05fde4
Source dataset
uspto-grants-1976_10
Patent number
US03985885

Reaction notes

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