Triphenylphosphine → HCID 18699969, compound

HRID 2288616Notes

Reaction equation

HRID 2288616 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:11]1([CH2:18][C:19]2[S:20][C:21]([C:24]([NH:26][NH2:27])=O)=[CH:22][CH:23]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.BrC(Cl)(Cl)C(Br)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.C(#N)C>[CH2:1]([NH:8][C:9]1[O:10][C:24]([C:21]2[S:20][C:19]([CH2:18][N:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:23][CH:22]=2)=[N:26][N:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 694261,2-Dibromo-1,1,2,2-tetrachloroethaneHCID 76639Benzyl isocyanateHCID 55213626HCID 55213626, compound

Product 1

HCID 18699969HCID 18699969, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

0.13 ml (1.05 mmol) of benzyl isocyanate was added to 25 ml of acetonitrile solution containing 253 mg (1.0 mmol) of 2-(hexahydro-1H-azepin-1-yl)methylthiophene-5-carboxylic acid hydrazide, and the mixture was stirred at room temperature for 40 hours, 718 mg (2.2 mmol) of 1,2-dibromo-1,1,2,2-tetrachloroethane, 1.22 ml of triethylamine and 1.16 g of triphenylphosphine were added, and then the mixture was stirred at room temperature for 9 hours. The reaction solution was concentrated, chloroform was added to the resulting residue, followed by washing with water and drying over anhydrous magnesium sulfate. The solvent was evaporated and the resulting residue was purified by a silica gel column chromatography to give 122 mg of the title compound in its free form. By subjecting 117 mg of this compound to salt formation using 27 mg of oxalic acid, 122 mg of the title compound was obtained.

Workup

  1. stirringthe mixture was stirred at room temperature for 9 hours
  2. concentrationThe reaction solution was concentrated
  3. additionchloroform was added to the resulting residue
  4. washby washing with water
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-b371c08c92584626815121af23bc7e69
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

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