Carbon Tetrachloride → Triphenylphosphine

HRID 1485015Notes

Reaction equation

HRID 1485015 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][NH:12][C:13]([C:15]2[N:16]=[CH:17][N:18]([CH3:30])[C:19](=[O:29])[C:20]=2[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:14])=O)=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)Cl.[CH:36]1[CH:41]=[CH:40][C:39]([P:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:38][CH:37]=1.CCN(CC)CC>CC#N.CCOC(C)=O>[CH2:22]([O:21][C:20]1[C:19](=[O:29])[N:18]([CH3:30])[CH:17]=[N:16][C:15]=1[C:13]1[O:14][C:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:11][N:12]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH:52]1[CH:51]=[CH:50][C:49]([P:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:39]2[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=2)=[CH:54][CH:53]=1

Participants

8

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 68225891HCID 68225891, compound

Product 2

HCID 11776TriphenylphosphineHCID 67446824HCID 67446824, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure described in European Patent No. 1698628, 5-benzyloxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid N′-[2-(4-fluoro-phenyl)-acetyl]-hydrazide was treated with CCl4 (7 equiv.), Ph3P (3 equiv.) and Et3N (3 equiv.) in CH3CN (10 vol) at room temperature for 1.5 h. TLC showed only one product formed. The reaction mixture was diluted with EtOAc, washed with aqueous NaHCO3 and brine, dried and concentrated to give a crude solid. For the 1.8 g scale reaction, chromatography (4 columns) plus recrystallization twice was needed to isolate the desired product without Ph3P═O contamination. NMR and MS confirmed the structure.

Workup

  1. customformed
  2. washwashed with aqueous NaHCO3 and brine
  3. customdried
  4. concentrationconcentrated
  5. customto give a crude solid
  6. customFor the 1.8 g scale reaction, chromatography (4 columns) plus recrystallization

Sources & evidence

ORD record
ord-14788baa583948cb80899bde8b984a61
Source dataset
uspto-grants-2016_08
Patent number
US09422282B2

Reaction notes

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