Vinylidene chloride → HCID 18361739, compound

HRID 1531779Notes

Reaction equation

HRID 1531779 reaction equation
C(O[C:4]1[O:8][N:7]=[C:6]([C:9]2[N:13]3[N:14]=[C:15]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[C:16]4[C:21]([C:12]3=[N:11][N:10]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:5]=1)C.C(N(CC)CC)C.C=C(Cl)[Cl:39]>ClCCl>[Cl:39][C:4]1[O:8][N:7]=[C:6]([C:9]2[N:13]3[N:14]=[C:15]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[C:16]4[C:21]([C:12]3=[N:11][N:10]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:5]=1

Participants

5

Reactant 3

HCID 6366Vinylidene chlorideHCID 8471TriethylamineHCID 18361767HCID 18361767, compound

Product 1

HCID 18361739HCID 18361739, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 70, part d) (50 mg, 0.14 mmol) was suspended in vinylidine chloride (5 ml) with triethylamine (43 mg, 0.42 mmol). The reaction was stirred for 16 hours, diluted with dichloromethane and washed with 5% ammonia solution and then dried (MgSO4), filtered and evaporated to yield a solid which was purified by preparative thin layer chromatography using methanol/dichloromethane (3:97) as elutant to yield 12.5 mg of pure product, 1H NMR (360 MHz, CDCl3) 8.66-8.72 (2H, m), 8.35 (1H, d, J=7 Hz), 7.98 (1H, t, J=7 Hz), 7.85 (1H, t, J=7 Hz), 7.80-7.70 (2H, m), 7.28 (1H, m), 7.03 (1H, s), 5.76 (2H, s); MS (ES30) 379 [MH]+.

Workup

  1. washwashed with 5% ammonia solution
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a solid which
  6. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-4b213857c6cb422da9576ab5a734e451
Source dataset
uspto-grants-2001_03
Patent number
US06200975B1

Reaction notes

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