Chlorosuccinimide → HCID 15456859, compound

HRID 1600558Notes

Reaction equation

HRID 1600558 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([C:9]2[CH:17]=[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:11]3[N:10]=2)=[C:4]([F:18])[CH:3]=1.[Cl:19]N1C(=O)CCC1=O>CN(C)C=O.O>[Cl:19][C:17]1[C:9]([C:5]2[CH:6]=[C:7]([OH:8])[C:2]([Cl:1])=[CH:3][C:4]=2[F:18])=[N:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=12

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 15456858HCID 15456858, compound

Product 1

HCID 15456859HCID 15456859, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

The product from Step C (8.3 g) was dissolved in dimethylformamide (40 ml) and was treated with N-chlorosuccinimide (4.4 g). The mixture was heated and at 65° C. a color change from yellow to red occurred. Heating was discontinued and the reaction was allowed to stir at room temperature overnight. The reaction mixture was diluted with water and ice and the solid was filtered and washed with water. After air drying the solid was taken up in ethyl acetate and dried further with magnesium sulfate. The ethyl acetate was removed by evaporation at reduced pressure to afford the product as a slightly pink solid (9.2 g), m.p.=177-178° C. NMR (DMSO-D6): δ 10.2 (OH), 7.3 (1H), 6.9 (1H), 3.9 (2H), 2.6 (2H), 1.9 (2H), 1.7 (2H).

Workup

  1. temperatureHeating
  2. filtrationthe solid was filtered
  3. washwashed with water
  4. customAfter air drying the solid
  5. dry with materialdried further with magnesium sulfate
  6. customThe ethyl acetate was removed by evaporation at reduced pressure

Sources & evidence

ORD record
ord-c9736383ac37401c854e94079b9c4f9f
Source dataset
uspto-grants-1999_11
Patent number
US05977028

Reaction notes

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