Sodium Carbonate → HCID 13827677, compound

HRID 1906065Notes

Reaction equation

HRID 1906065 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([NH:14][OH:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[CH2:17][C:18]1[C:23]([CH3:24])=[C:22]([CH2:25]Cl)[C:21]([CH3:27])=[C:20]([CH2:28]Cl)[C:19]=1[CH3:30]>CN(C)C=O>[CH2:7]([N:14]([CH2:17][C:18]1[C:23]([CH3:24])=[C:22]([CH2:25][N:14]([OH:15])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:21]([CH3:27])=[C:20]([CH2:28][N:14]([OH:15])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:19]=1[CH3:30])[OH:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2911881,3,5-Tris(chloromethyl)-2,4,6-trimethylbenzeneHCID 2794173Benzylhydroxylamine

Product 1

HCID 13827677HCID 13827677, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 3.87 g of sodium carbonate in 30 ml of dry N,N-dimethylformamide is added 4.50 g of N-benzylhydroxylamine followed by 3.23 g of 2,4,6-tris(chloromethyl)mesitylene. After stirring at 80° C. for 8 hours, dimethylformamide is removed under reduced pressure and the residue is partitioned between methylene chloride and water. The combined organic layers are washed with water, brine, dried and evaporated to give a crude product. Recrystallization from ethyl acetate-heptane affords 4.0 g of white solid, mp 193°-195° C.

Workup

  1. customdimethylformamide is removed under reduced pressure
  2. customthe residue is partitioned between methylene chloride and water
  3. washThe combined organic layers are washed with water, brine
  4. customdried
  5. customevaporated
  6. customto give a crude product
  7. customRecrystallization from ethyl acetate-heptane

Sources & evidence

ORD record
ord-b7d29d8a29ca4ed8aa18768c3291aa3a
Source dataset
uspto-grants-1987_03
Patent number
US04649221

Reaction notes

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