Carbon Tetrachloride → HCID 58148021, compound

HRID 1879931Notes

Reaction equation

HRID 1879931 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]=[C:17]3[CH:33]=[CH:32][C:31]([CH2:34][N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)=[CH:30][N:18]3[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.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.O>[CH2:22]([O:21][C:20]1[C:19](=[O:29])[N:18]2[CH:30]=[C:31]([CH2:34][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH:32]=[CH:33][C:17]2=[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

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66953358HCID 66953358, compound

Product 1

HCID 58148021HCID 58148021, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The product of example 16 (250 mg, 0.46 mmol), carbon tetrachloride (354 mg, 2.3 mmol) and triethylamine (116 mg, 1.15 mmol) were mixed in acetonitrile (15 ml). To the above mixture was added triphenylphosphine (302 mg, 1.15 mmol) at room temperature and stirred overnight. Then water (50 ml) was added and the mixture was extracted with dichloromethane three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and evaporated into dryness. The residue was subjected to silica gel chromatography using PE-ethyl acetate (1:4 v/v) as eluent to give the titled product (195 mg, 80.7%).

Workup

  1. extractionthe mixture was extracted with dichloromethane three times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated into dryness

Sources & evidence

ORD record
ord-e9b217c4325944dbbc530388061bf9a4
Source dataset
uspto-grants-2012_11
Patent number
US08318732B2

Reaction notes

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