Chloromethyl ethyl ether → HCID 59488853, compound

HRID 2274358Notes

Reaction equation

HRID 2274358 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][C:4]=1[N+:19]([O-:21])=[O:20].[H-].[Na+].[CH2:24]([O:26][CH2:27]Cl)[CH3:25]>C1COCC1>[N+:19]([C:4]1[CH:5]=[C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([O:18][CH2:27][O:26][CH2:24][CH3:25])[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:7]=[CH:8][C:3]=1[NH:2][CH3:1])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 59488860HCID 59488860, compound

Product 1

HCID 59488853HCID 59488853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 3 necked 250 ml round bottom flask was dried in an oven at 80° C. overnight. A suspension of 6 (16.6 mmol, 5 g) in dry THF (180 ml) has been poured drop wise into a suspension of NaH 60% dispersion in mineral oil (33.2 mmol, 1.26 g, 2 eq) in dry THF (20 ml). Once the addition was complete neat ethoxy methyl chloride (16.6 mmol, 1.54 ml, 1 eq) was added and the reaction stirred over night. The dark brown mixture was filtrated under vacuum and the filtrate concentrated under high vacuum.

Workup

  1. customA 3 necked 250 ml round bottom flask was dried in an oven at 80° C. overnight
  2. additionhas been poured drop
  3. additionOnce the addition
  4. additionwas added
  5. filtrationThe dark brown mixture was filtrated under vacuum
  6. concentrationthe filtrate concentrated under high vacuum

Sources & evidence

ORD record
ord-5da58ac2a1804d12ad81bbfaf447bf03
Source dataset
uspto-grants-2015_09
Patent number
US09126961B2

Reaction notes

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