Water → HCID 12781935, compound

HRID 918070Notes

Reaction equation

HRID 918070 reaction equation
[N:1]1([CH2:7][C:8]2[S:12][C:11]([C:13]3[O:14][C:15]4[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:16]=4[N:17]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.C(=O)([O-])[O-].[Ca+2].[C:31](Cl)(Cl)=[S:32]>O1CCCC1.C(Cl)(Cl)Cl.[Pt]=O>[N:22]([C:19]1[CH:20]=[CH:21][C:15]2[O:14][C:13]([C:11]3[S:12][C:8]([CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:9][CH:10]=3)=[N:17][C:16]=2[CH:18]=1)=[C:31]=[S:32]

Participants

8

Reactant 4

HCID 962WaterHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 127819302-{5-[(Morpholin-4-yl)methyl]thiophen-2-yl}-5-nitro-1,3-benzoxazole

Product 1

HCID 12781935HCID 12781935, compoundYield 21.3%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[5-(4-morpholinylmethyl)-2-thienyl]-5-nitrobenzoxazole (1.75 g, 0.005 mole) in 50 ml of tetrahydrofuran, 0.2 g of platinum oxide is added. The mixture is hydrogenated at 50 psi over a period of 3 hours. The catalyst is removed by filtration and the solvent is evaporated under vacuum yielding an oil. The oil is dissolved in 25 ml of chloroform and added slowly to the following mixture at 10°C: water 25 ml; calcium carbonate 1.2 g, 0.012 mole; thiophosgene 0.6 g, 0.005 mole; and chloroform 25 ml. The reaction mixture is then stirred overnight at room temperature. The chloroform layer is separated, dried over anhydrous magnesium sulfate and evaporated under vacuum yielding a solid. Crystallization from petroleum ether yields 0.380 g of the title compound, melting point 135°-138°C.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent is evaporated under vacuum
  3. customyielding an oil
  4. additionadded slowly to the following mixture at 10°C
  5. customThe chloroform layer is separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under vacuum
  8. customyielding a solid
  9. customCrystallization from petroleum ether

Sources & evidence

ORD record
ord-c99a6d3ae44947b9b803f9c5af90382d
Source dataset
uspto-grants-1976_07
Patent number
US03969351

Reaction notes

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