Sodium Chloride → HCID 21901780, compound

HRID 719738Notes

Reaction equation

HRID 719738 reaction equation
S(Cl)(C)(=O)=O.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH2:17][CH:16]2[CH2:20]O)=[CH:11][CH:10]=1)([O-:8])=[O:7].C(N(CC)CC)C.[Cl-:29].[Na+]>CN(C=O)C>[Cl:29][CH2:20][CH:16]1[CH2:17][CH2:18][CH2:19][N:15]1[C:12]1[CH:13]=[CH:14][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6056432-Pyrrolidinemethanol, 1-(4-nitrophenyl)-

Product 1

HCID 21901780HCID 21901780, compoundYield 882.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

27.9 ml (0.36 mol) of mesyl chloride were added dropwise to a solution of [1-(4-nitrophenyl)pyrrolidin-2-yl]methanol (66.7 g, 0.03 mol), 300 ml of anhydrous DMF and 58.5 ml (0.42 mol) of anhydrous triethylamine, cooled in an ice bath. The temperature was allowed to rise to 20° C. over one hour with stirring. 35.2 g (0.6 mol) of sodium chloride were added and the mixture was heated at 100° C. for one hour. The reaction medium was poured into 1.4 l of ice-water. The precipitate was filtered off, washed with water, dried and recrystallized from isopropanol. 63.7 g of a yellow powder (1) were thus obtained.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried
  5. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-db83a59d84f545d3a4a2b3b805ca0889
Source dataset
uspto-grants-2006_11
Patent number
US07132543B2

Reaction notes

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