Water → HCID 59129756, compound

HRID 1991470Notes

Reaction equation

HRID 1991470 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[S:15][CH2:14][CH2:13][S:12]1.[H-].[Na+].Br[CH2:19][C:20]([NH2:22])=[O:21].O>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:19][C:20]([NH2:22])=[O:21])[C:6](=[O:11])[C:5]12[S:12][CH2:13][CH2:14][S:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 1262426HCID 1262426, compound

Product 1

HCID 59129756HCID 59129756, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Compound 6 (8 g, 33.7 mmol) was dissolved in dry DMF (80 ml) under a nitrogen atmosphere. The solution was cooled at 0° C. and NaH (1.62 g, 37.13 mmol, 60% dispersion) was carefully added portionwise. When the nitrogen evolution ceased, bromoacetamide (5.6 g, 37.13 mmol) was added. After 30 minutes, the mixture was poured into cold water and the solid filtered off, washed with water and hexane. The crude material was directly crystallized in acetonitrile affording 2-[5′-methyl-2′-oxospiro[1,3-dithiolane-2,3′-indol]-1′(2′H)-yl]acetamide 15 as a white solid.

Workup

  1. filtrationthe solid filtered off
  2. washwashed with water and hexane
  3. customThe crude material was directly crystallized in acetonitrile

Sources & evidence

ORD record
ord-fa34d07e112b45be942d1fbffb814b1a
Source dataset
uspto-grants-2010_01
Patent number
US07645887B2

Reaction notes

Loading…