Sodium Sulfide → HCID 59279591, compound

HRID 1921211Notes

Reaction equation

HRID 1921211 reaction equation
[S-2:1].[Na+].[Na+].[Br:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]2([CH2:18][CH2:19]Br)[CH2:15][CH2:16]Br>CN(C=O)C>[Br:4][C:5]1[CH:6]=[C:7]2[C:8]3([CH2:18][CH2:19][S:1][CH2:16][CH2:15]3)[C:9](=[O:14])[NH:10][C:11]2=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 59279593HCID 59279593, compound

Product 1

HCID 59279591HCID 59279591, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium sulfide (292 mg, 3.75 mmol) was added to a solution of 5-bromo-3,3-bis(2-bromoethyl)-1,3-dihydro-2H-indol-2-one from Step B (532 mg, 1.25 mmol) in DMF (2 mL) and the solution heated to 50° C. After 2.5 h, the mixture was partitioned between CH2Cl2 (20 mL) and H2O (20 mL). The layers were separated and the aqueous layer was further extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=300 (M+1).

Workup

  1. customthe mixture was partitioned between CH2Cl2 (20 mL) and H2O (20 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with CH2Cl2 (2×10 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5aac588e20a246fd90d967990feef5d5
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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