Water → HCID 18921415, compound

HRID 1289365Notes

Reaction equation

HRID 1289365 reaction equation
[F:1][C:2]1[C:21]([NH2:22])=[C:6]2[CH2:7][S:8](=[O:20])(=[O:19])[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[C:5]2=[CH:4][CH:3]=1.[Cl:23]N1C(=O)CCC1=O.CCOCC.O>CN(C)C=O>[Cl:23][C:4]1[CH:3]=[C:2]([F:1])[C:21]([NH2:22])=[C:6]2[C:5]=1[N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[S:8](=[O:20])(=[O:19])[CH2:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 31398ChlorosuccinimideHCID 18921413HCID 18921413, compound

Product 1

HCID 18921415HCID 18921415, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the title compound of Step C (0.387 g, 1.2 mmol) and N-chlorosuccinimide (0.168 g, 1.26 mmol) in dimethylformamide (6 mL) was heated at 80° C. for 4 h. After completion of the reaction, the mixture was poured into a mixture of ether (25 mL) and water (10 mL). The organic phase was separated, dried (MgSO4) and the solvent was removed on a rotary evaporator. Flash chromatography of the resulting residue afforded 0.4 g of the title compound of Step D. 1H NMR (CDCl3, 400 MHz): δ7.23 (d,2H), 7.03 (d,1H), 6.74 (d,2H), 4.93 (s,2H), 3.84 (s,2H), 3.75 (s,3H).

Workup

  1. customAfter completion of the reaction
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-00fe4e7117af4c2d9da1871906a1f867
Source dataset
uspto-grants-1998_05
Patent number
US05750471

Reaction notes

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