Sodium hydride → HCID 57141444, compound

HRID 1395690Notes

Reaction equation

HRID 1395690 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[O:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1.Cl.[CH3:24][N:25]([CH2:27][CH2:28]Cl)[CH3:26].C(O)(=O)/C=C\C(O)=O>CN(C)C=O.O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[O:11][CH2:12][C:13]([O:15][CH2:28][CH2:27][N:25]([CH3:26])[CH3:24])=[O:14])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 444266Maleic AcidHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 18347834HCID 18347834, compound

Product 1

HCID 57141444HCID 57141444, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.32 g., 80% w/w dispersion in mineral oil) was added in portions to a solution of di-(4-chlorophenyl)methyloxyacetic acid (6.2 g.) in dry dimethylformamide (30 ml.) cooled below 30°. The mixture was stirred for 15 minutes at ambient temperature after the addition was complete and N,N-dimethyl-2-chloroethylamine hydrochloride (2.88 g.) was then added. The mixture was heated at 100° for 16 hours, cooled and then poured into water (200 ml.). The aqueous mixture was extracted with ether. The extracts were washed with aqueous acetic acid (2×100 ml. of a 10% v/v solution). The acid washings were basified to pH 11-12 with aqueous sodium hydroxide solution and extracted with ether. The ether extracts were dried (MgSO4) and evaporated. The residual oil thus obtained was mixed with an excess of an ethereal solution of maleic acid. The solid thus formed was separated by filtration and crystallised from ethyl acetate to give 2-dimethylamino-ethyl di-(4-chlorophenyl)methyloxyacetate as the maleate salt, m.p. 103°-104°, having the composition C19H21O3NCl2.C4H4O4 by microanalysis, and in 43% yield.

Workup

  1. temperaturecooled below 30°
  2. additionafter the addition
  3. temperatureThe mixture was heated at 100° for 16 hours
  4. temperaturecooled
  5. extractionThe aqueous mixture was extracted with ether
  6. washThe extracts were washed with aqueous acetic acid (2×100 ml
  7. extractionextracted with ether
  8. dry with materialThe ether extracts were dried (MgSO4)
  9. customevaporated
  10. customThe residual oil thus obtained
  11. customThe solid thus formed
  12. customwas separated by filtration
  13. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-902e30bcd3a8412b944d2f316913a50a
Source dataset
uspto-grants-1980_05
Patent number
US04205087

Reaction notes

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