Sodium Hydroxide → 1-(1-Methylpyrrolidin-2-ylidene)-3-(p-nitrophenyl)urea

HRID 1973923

Reaktionsgleichung

Reaktionsgleichung von HRID 1973923
Cl.[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[NH:8].[OH-].[Na+].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1)([O-:13])=[O:12].[N-]=C=O>C1C=CC=CC=1.O>[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[N:8][C:21]([NH:20][C:17]1[CH:16]=[CH:15][C:14]([N+:11]([O-:13])=[O:12])=[CH:19][CH:18]=1)=[O:22]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 66012Benzene, 1-isocyanato-4-nitro-HCID 105034IsocyanateHCID 124489671-Methylpyrrolidin-2-imine hydrochloride

Produkt 1

HCID 30393631-(1-Methylpyrrolidin-2-ylidene)-3-(p-nitrophenyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 6.73 g. (0.05 mole) of 1 -methyl-2 -iminopyrrolidine hydrochloride in 100 ml. of benzene is added 2 ml. of water followed by 5 ml. of 50 % NaOH. After stirring for 5 min., the benzene layer is decanted onto excess anhydrous potassium carbonate. The process is repeated twice with 75 ml. portions of fresh benzene. The combined extracts are filtered rapidly from drying agent (dicalite pad and suction). To the filtrate is added in one portion with stirring 8.21 g. (0.05 mole) of p-nitrophenylisocyanate as a solution in benzene (the isocyanate solution is filtered prior to use). After stirring one hour, the solid, 1 -(1 -methyl-2 -pyrrolidylidene)-3 -p-nitrophenylurea, is collected and dried, m.p. = 180°-182° C. Recrystallization from acetone-methanol gives pure product, m.p. = 182°-183° C.

Aufarbeitung

  1. additionTo a suspension of 6.73 g
  2. customthe benzene layer is decanted onto excess anhydrous potassium carbonate
  3. filtrationThe combined extracts are filtered rapidly
  4. dry with materialfrom drying agent (dicalite pad and suction)
  5. additionTo the filtrate is added in one portion
  6. stirringwith stirring 8.21 g
  7. stirringAfter stirring one hour
  8. customthe solid, 1 -(1 -methyl-2 -pyrrolidylidene)-3 -p-nitrophenylurea, is collected
  9. customdried
  10. customRecrystallization from acetone-methanol
  11. customgives pure product, m.p. = 182°-183° C.

Quellen und Nachweise

ORD-Eintrag
ord-1688382b48a44fee8902cb2b3daf81b0
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03998958

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