Ethanol → 5-Isothiocyanato-2-(5-methylfuran-2-yl)-1,3-benzoxazole

HRID 1287663Notes

Reaction equation

HRID 1287663 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[O:13][C:14]([CH3:17])=[CH:15][CH:16]=3)=[N:9][C:8]=2[CH:18]=1)([O-])=O.CCO.[C:22](Cl)(Cl)=[S:23].C(=O)([O-])[O-].[Ca+2]>C(Cl)(Cl)Cl.[Pd].O>[CH3:17][C:14]1[O:13][C:12]([C:10]2[O:11][C:7]3[CH:6]=[CH:5][C:4]([N:1]=[C:22]=[S:23])=[CH:18][C:8]=3[N:9]=2)=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 127819142-(5-Methylfuran-2-yl)-5-nitro-1,3-benzoxazole

Product 1

HCID 127819235-Isothiocyanato-2-(5-methylfuran-2-yl)-1,3-benzoxazoleYield 420.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

3.32 g (0.0013 mole) of 5-nitro-2-(5-methyl-2-furyl)benzoxazole and 0.65 g of 10% Pd are suspended in 100 ml of abs. EtOH and hydrogenated at 65 psi over a period of 4 hr. The catalyst is removed and the EtOH evaporated under vacuum yielding a dark brown residue. The residue is dissolved in 150 ml of CHCl3 and added dropwise to the following cold suspension: 1.5 g (0.013 mole) of thiophosgene, 1.3 g (0.013 mole) of calcium carbonate, 150 ml of CHCl3 and 30 ml of water. After the addition is complete the mixture is warmed to room temperature and allowed to stir overnight. The CHCl3 layer is then separated and evaporated to dryness yielding 1.4 g of a light brown solid (43%) mp 110°-121°. This material is then extracted with petroleum ether and the extracts then evaporated yielding a tan solid. This material is recrystallized from petroleum ether yielding 0.540 g of white powder, mp 130°-132° (16%).

Workup

  1. customThe catalyst is removed
  2. customthe EtOH evaporated under vacuum
  3. customyielding a dark brown residue
  4. additionadded dropwise to the following cold suspension
  5. additionAfter the addition
  6. customThe CHCl3 layer is then separated
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-e4d3e52f244448639ea3ba24871406e5
Source dataset
uspto-grants-1976_10
Patent number
US03985755

Reaction notes

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