Methyl bromoacetate → HCID 54122834, compound

HRID 703813Notes

Reaction equation

HRID 703813 reaction equation
[CH3:1][NH:2][C:3](=[O:12])[NH:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]([NH:4][N:5]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:12]

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 288314N-Methyl-2-phenylhydrazine-1-carboximidic acid

Product 1

HCID 54122834HCID 54122834, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-methyl-1-phenylsemicarbazide (20.0 g), methyl bromoacetate (27.75 g) and diisopropylethylamine (23.2 ml) in toluene (200 ml) under nitrogen was heated at 90° to 100° for 25 h with stirring. Toluene (120 ml) was then distilled off at ca. 90° under reduced pressure. The mixture was cooled to <50° and diluted with water (120 ml) and ethyl acetate (200 ml). The organic phase was separated and washed with water (60 ml). The two aqueous phases were extracted sequentially with ethyl acetate (2×60 ml). The combined organic phases were filtered and concentrated to 80 ml at atmospheric pressure. Toluene (100 ml) was added and the solution was again concentrated to 80 ml. The concentrate was seeded at ca. 80° with an authentic sample of the title compound, and allowed to cool to ca. 20° overnight. The resultant solid was filtered off, washed with toluene (20 ml) followed by t-butyl methyl ether (20 ml), and dried in vacuo for 24 h to give the title compound (22.39 g), m.p. 122°-122.5°.

Workup

  1. temperaturewas heated at 90° to 100° for 25 h
  2. distillationToluene (120 ml) was then distilled off at ca. 90° under reduced pressure
  3. temperatureThe mixture was cooled to <50°
  4. additiondiluted with water (120 ml) and ethyl acetate (200 ml)
  5. customThe organic phase was separated
  6. washwashed with water (60 ml)
  7. extractionThe two aqueous phases were extracted sequentially with ethyl acetate (2×60 ml)
  8. filtrationThe combined organic phases were filtered
  9. concentrationconcentrated to 80 ml at atmospheric pressure
  10. additionToluene (100 ml) was added
  11. concentrationthe solution was again concentrated to 80 ml
  12. customwas seeded at ca. 80° with an authentic sample of the title compound
  13. temperatureto cool to ca. 20° overnight
  14. filtrationThe resultant solid was filtered off
  15. washwashed with toluene (20 ml)
  16. customdried in vacuo for 24 h

Sources & evidence

ORD record
ord-7e75a1566476401ebcd6773dabf1d04e
Source dataset
uspto-grants-1991_01
Patent number
US04985427

Reaction notes

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