Triphosgene → HCID 136338031, compound

HRID 707468Notes

Reaction equation

HRID 707468 reaction equation
[NH2:1][C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][C:3]=1[C:9]1[NH:13][N:12]=[CH:11][CH:10]=1.Cl[C:15]([O:18]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl>C1(C)C=CC=CC=1.C1COCC1>[O:18]=[C:15]1[N:13]2[N:12]=[CH:11][CH:10]=[C:9]2[C:3]2[CH:4]=[C:5]([CH:7]=[O:8])[S:6][C:2]=2[NH:1]1

Participants

5

Reactant 2

HCID 94429TriphosgeneHCID 86705380HCID 86705380, compound

Product 1

HCID 136338031HCID 136338031, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-4-(1H-pyrazol-5-yl)thiophene-2-carbaldehyde (12 mg, 0.06 mmol) and bis(trichloromethyl)carbonate (55 mg, 0.19 mmol) were dissolved in toluene (3 mL) and THF (0.5 mL), and the reaction heated in a sealed tube at 100° C. for 3 h. The reaction was cooled to room temperature, hexanes (10 mL) added, suspension stirred at room temperature for 30 min, precipitate washed with additional hexanes (10 mL), dried under reduced pressure to yield 5-oxo-4,5-dihydropyrazolo[1,5-c]thieno[3,2-e]pyrimidine-2-carbaldehyde as a powder (11 mg, 81%). 1H NMR (400 MHZ, DMSO-d6) δ 6.99 (s, 1H), 8.12 (s, 1H), 8.45 (s, 1H), 9.93 (s, 1H), 13.06 (s, 1H).

Workup

  1. washprecipitate washed with additional hexanes (10 mL)
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-ceae5451314c4454b42bf15150ab3764
Source dataset
uspto-grants-2015_11
Patent number
US09175010B2

Reaction notes

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