Diethyl Ether → HCID 22120827, compound

HRID 703797Notes

Reaction equation

HRID 703797 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-:17].[Na+].[CH3:21][CH2:22][O:23][CH2:24]C>ClCC(OC)=O>[CH3:24][O:23][C:22](=[O:17])[CH2:21][NH:12][C:11]1[CH:13]=[CH:14][CH:15]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 928923-BenzyloxyanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 22120827HCID 22120827, compound

Reagents, catalysts & solvents 1

HCID 7295Methyl chloroacetateSolvent

Procedure

A suspension of 3-benzyloxyaniline (69.0 g) and sodium bicarbonate (58.1 g) in methyl chloroacetate (45.4 ml) was stirred at 80°-90° under nitrogen for 16 h. The resultant solid was poured into ether (400 ml) and the suspension was filtered. The collected solid was partitioned between water (400 ml) and dichloromethane (200 ml). The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×200 ml). The combined organic extracts were dried and concentrated to give the title compound (66.9 g) as a solid, m.p. 92°-94°.

Workup

  1. filtrationthe suspension was filtered
  2. customThe collected solid was partitioned between water (400 ml) and dichloromethane (200 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×200 ml)
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e90892a16b0474684ef3954b93bef56
Source dataset
uspto-grants-1991_01
Patent number
US04985427

Reaction notes

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