Water → HCID 18779697, compound

HRID 1421698Notes

Reaction equation

HRID 1421698 reaction equation
[Br:1]N1C(=O)CCC1=O.CSC.[Cl:12][C:13]1[CH:14]=[CH:15][C:16](=[O:27])[N:17]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=2)[CH:18]=1.O>C(Cl)Cl>[Br:1][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([N:17]2[CH:18]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]2=[O:27])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 67184N-bromobutanimideHCID 18779701HCID 18779701, compound

Product 1

HCID 18779697HCID 18779697, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

To N-bromosuccinimide (0.166 g, 0.929 mmol) in CH2Cl2 (3 mL) at 0° C. was added dimethylsulfide (0.082 mL, 1.11 mmol). The resulting suspension was cooled to -20° C. and a solution of the alcohol from Step 1 (0.146 g, 0.62 mmol) in CH2Cl2 was added dropwise over 2 minutes. The reaction mixture was stirred at 0° C. for 6 hrs and then poured into water and extracted with CH2Cl2. The extracts were dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc: CH2Cl2 1:1 as eluent) to afford the title compound as a white solid.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe extracts were dried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was chromatographed (silica gel, EtOAc: CH2Cl2 1:1 as eluent)

Sources & evidence

ORD record
ord-8afd2f6c0ea94ff09d3d146f2358ad30
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

Loading…