Water → Xilobam

HRID 1973930Notes

Reaction equation

HRID 1973930 reaction equation
Cl.[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[NH:8].O.[OH-].[Na+].[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[N:20]=[C:21]=[O:22]>C1C=CC=CC=1>[CH3:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH3:12])[C:14]=1[NH:20][C:21]([N:8]=[C:4]1[CH2:5][CH2:6][CH2:7][N:3]1[CH3:2])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 987872,6-Xylyl isocyanateHCID 124489671-Methylpyrrolidin-2-imine hydrochloride

Product 1

HCID 39689Xilobam

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirring solution of 6.73 g. (0.05 mole) of 1-methyl- 2-iminopyrrolidine hydrochloride in about 2 ml. of water is added about 50 ml. of benzene followed by 10 ml. of 50% NaOH. After stirring 1 min. the benzene layer is decanted onto anhydrous potassium carbonate. The extraction is repeated twice. The combined benzene extracts are filtered from a drying agent (dicalite pad) and rinsed well with dry benzene. To the filtrate is added in one portion with stirring 7.36 g. (0.05 mole) of 2,6-dimethylphenylisocyanate. The reaction mixture is stirred overnight. Solvent removal and recrystallization from ethyl acetate-ether gives the product, 1-(2,6 -dimethylphenyl)-3-(1-methyl-2-pyrrolidylidene)urea, as white crystals, m.p. = 119°-120° C.

Workup

  1. customis decanted onto anhydrous potassium carbonate
  2. extractionThe extraction
  3. filtrationThe combined benzene extracts are filtered from a drying agent (dicalite pad)
  4. washrinsed well with dry benzene
  5. additionTo the filtrate is added in one portion
  6. stirringThe reaction mixture is stirred overnight
  7. customSolvent removal and recrystallization from ethyl acetate-ether

Sources & evidence

ORD record
ord-c9c45004406b44bfbb0dfc6151186571
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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