Chloroacetonitrile → HCID 57754432, compound

HRID 226262Notes

Reaction equation

HRID 226262 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]3[O:28][CH2:27][C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[CH:20](O)[C:19]=3[CH:30]=1)[CH:6]=[CH:5]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1.Cl[CH2:54][C:55]#[N:56].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]3[O:28][CH2:27][C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[CH:20]([S:40][CH2:54][C:55]#[N:56])[C:19]=3[CH:30]=1)[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 87949Lawesson's reagentHCID 57754454HCID 57754454, compound

Product 1

HCID 57754432HCID 57754432, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.3 g (0.74 mmol) of the product from Example 1, step 6 and 0.3 g (0.74 mmol) of Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) in 30 ml of toluene is refluxed for 15′. The solution is washed with water, dried and concentrated. The residue is dissolved in 25 ml of dichloromethane and 0.07 g (0.93 mmol) of chloroacetonitrile and 0.14 ml (0.10 g; 1.0 mmol) of N,N,N-triethylamine are added. The whole is stirred overnight at room temperature. The solution is washed with water, dried, concentrated and chromatographied trough SiO2 eluting with dichloromethane/methanol 98:2. The yield of title product is 0.12 g (35%).

Workup

  1. temperatureis refluxed for 15′
  2. washThe solution is washed with water
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in 25 ml of dichloromethane
  6. washThe solution is washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5d41f26482b5487fa2245b1627ca4403
Source dataset
uspto-grants-2009_07
Patent number
US07557212B2

Reaction notes

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