1,2-Dichloroethane → HCID 15391112, compound

HRID 1280439Notes

Reaction equation

HRID 1280439 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([N:13]1[C:17]2=[N:18][CH:19]=[N:20][CH:21]=[C:16]2[C:15]([C:22]2[O:23]C=[CH:25][CH:26]=2)=[N:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[N+](C)=CCl.[Cl-].[OH:33]P([O-])([O-])=O.[K+].[K+].Cl[CH2:41][CH2:42]Cl>CN(C=O)C>[CH2:6]([N:13]1[C:17]2=[N:18][CH:19]=[N:20][CH:21]=[C:16]2[C:15]([C:22]2[O:23][C:41]([CH:42]=[O:33])=[CH:25][CH:26]=2)=[N:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 111,2-Dichloroethane2×HCID 24450Potassium Phosphate, DibasicHCID 24813Phosphorus oxychloride2×HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 15391110HCID 15391110, compound

Product 1

HCID 15391112HCID 15391112, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

0.74 ml of POCl3 is added at 0° C. to 0.64 ml of DMF. The solidified mixture is allowed to come to room temperature and 14 ml of 1,2-dichloroethane are added. A solution of 2 g of 1-benzyl-3-(2-furyl)pyrazolo[3,4-d]pyrimidine (Rf=0.45, SiO2, toluene/ethyl acetate=1:1) in 14 ml of 1,2-dichloroethane is added dropwise at 15° C. to this solution and it is then warmed to 80° C. After 4 h, the entire batch is added dropwise to further Vilsmeier reagent, which was prepared from 1.5 ml of POCl3 and 1.3 ml of DMF, and stirred at 80° C. for 24 h. The mixture is then added to a 50% aqueous solution of K2HPO4 and briefly heated to 75° C. with stirring. After extraction with ethyl acetate, drying of the organic phase, concentration in a rotary evaporator and chromatography on SiO2, 0.6 g (27% of theory) of an oil is obtained (Rf=0.3, SiO2, toluene/ethyl acetate=1:1).

Workup

  1. customto come to room temperature
  2. temperaturebriefly heated to 75° C.
  3. stirringwith stirring
  4. extractionAfter extraction with ethyl acetate
  5. customdrying of the organic phase, concentration in a rotary evaporator and chromatography on SiO2, 0.6 g (27% of theory) of an oil
  6. customis obtained (Rf=0.3, SiO2, toluene/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-55bbedc012114777b33272b99a8d4f74
Source dataset
uspto-grants-2002_09
Patent number
US06451805B1

Reaction notes

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