Carbon Tetrachloride → HCID 24993977, compound

HRID 558172Notes

Reaction equation

HRID 558172 reaction equation
[C:1]1([NH:7][C:8](=[O:27])[NH:9][NH:10][C:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>C(OCC)(=O)C.O1CCCC1.C(Cl)Cl>[C:1]1([NH:7][C:8]2[O:27][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH2:19][C:20]3[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=3)=[N:10][N:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 59152568HCID 59152568, compound

Product 1

HCID 24993977HCID 24993977, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-phenyl-1-(2-(pyridin-4-yl) methoxybenzoyl) semicarbazide (110 mg, 0.47 mmol; Reference Compound 6-(1) and triphenylphosphine (190 mg, 0.71 mmol) in a mixed solvent of methylene chloride (3.0 mL) and tetrahydrofuran (3.0 mL) were added carbon tetrachloride (290 mg, 1.9 mmol) and triethylamine (70 mg, 0.71 mmol), and then the mixture was refluxed overnight. The reaction solution was cooled to room temperature and ethyl acetate was added thereto. The ethyl acetate solution was washed with a saturated brine solution. To the solution was added a 1M hydrochloric acid and then the aqueous layer was taken out. To the aqueous layer was added a 1 M aqueous sodium hydroxide solution. The solid which precipitated at pH 8 was filtered off and dried under a reduced pressure to give 65 mg (40%) of the titled compound as a colorless solid.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. washThe ethyl acetate solution was washed with a saturated brine solution
  3. additionTo the solution was added a 1M hydrochloric acid
  4. additionTo the aqueous layer was added a 1 M aqueous sodium hydroxide solution
  5. customThe solid which precipitated at pH 8
  6. filtrationwas filtered off
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-d68bb60e05144e7b99a4d25e525fccb8
Source dataset
uspto-grants-2011_11
Patent number
US08063034B2

Reaction notes

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