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

HRID 1973923노트

반응식

HRID 1973923 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매2회HCID 962Water용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-1688382b48a44fee8902cb2b3daf81b0
출처 데이터셋
uspto-grants-1976_12
특허 번호
US03998958

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