Glycine ethyl ester → HCID 21285524, compound

HRID 2231653Notes

Reaction equation

HRID 2231653 reaction equation
[NH2:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:8][C:9]1[C:16]([CH3:17])=[CH:15][C:14]([I:18])=[CH:13][C:10]=1[CH:11]=O>C(Cl)(Cl)Cl>[NH2:8][C:9]1[C:16]([CH3:17])=[CH:15][C:14]([I:18])=[CH:13][C:10]=1[CH2:11][NH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 12176Glycine ethyl esterHCID 212855162-Amino-5-iodo-3-methylbenzaldehyde

Product 1

HCID 21285524HCID 21285524, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of freshly prepared ethyl glycinate (2.58 g), 2-amino-5-iodo-3-methylbenzaldehyde (4.03 g) and 3Å molecular sieves (2 g "Fluka A.G." [Trade Mark] article No. 69828) was heated with stirring under reflux in chloroform (50 cm3) for 4 hours. The cooled solution was filtered, evaporated in vacuo, and the residue taken into ethanol (30 cm3) and treated with sodium cyanoborohydride (1.43 g). After stirring for 72 hours ethanol was removed in vacuo and the residue was partitioned between chloroform (50 cm3) and aqueous ammonia (50 cm3, S.G. 0.88). The aqueous phase was further extracted with chloroform (2×100 cm3) and the combined organic extracts were dried (MgSO4) and evaporated to give the title compound as a crude oil, (2.5 g).

Workup

  1. temperature69828) was heated
  2. filtrationThe cooled solution was filtered
  3. customevaporated in vacuo
  4. additiontreated with sodium cyanoborohydride (1.43 g)
  5. stirringAfter stirring for 72 hours ethanol
  6. customwas removed in vacuo
  7. customthe residue was partitioned between chloroform (50 cm3) and aqueous ammonia (50 cm3, S.G. 0.88)
  8. extractionThe aqueous phase was further extracted with chloroform (2×100 cm3)
  9. dry with materialthe combined organic extracts were dried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-7730e126de544f6dbe4de3a940aea8b3
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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