Hydrochloric Acid → N-(2-chloromethoxyethyl)phthalimide

HRID 614950Notes

Reaction equation

HRID 614950 reaction equation
O[CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[CH2:15]=[O:16].[ClH:17]>ClCCCl>[Cl:17][CH2:15][O:16][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 77499N-(2-Hydroxyethyl)phthalimide

Product 1

HCID 12926790N-(2-chloromethoxyethyl)phthalimide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A dispersion of N-(2-hydroxyethyl)phthalimide (19.1 g) and paraformaldehyde (3.0 g) in 1,2-dichloroethane (250 ml) was cooled in an ice-salt-acetone bath and saturated with dry hydrochloric acid with stirring. After 4 hours the mixture was dried over calcium chloride, filtered and evaporated under reduced pressure to give N-(2-chloromethoxyethyl)phthalimide (21.9 g), m.p. 69°-72° C.

Workup

  1. dry with materialAfter 4 hours the mixture was dried over calcium chloride
  2. filtrationfiltered
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c378482662184ae28c1ed8b3960166d6
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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