Methyl Isocyanate → HCID 20068373, compound

HRID 1638261Notes

Reaction equation

HRID 1638261 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[N:12]1[C:16]([CH2:17][NH2:18])=[CH:15][N:14]=[CH:13]1.[N:20]([CH3:23])=[C:21]=[O:22]>ClC(Cl)Cl>[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[N:12]1[C:16]([CH2:17][NH:18][C:21]([NH:20][CH3:23])=[O:22])=[CH:15][N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 20068400HCID 20068400, compound

Product 1

HCID 20068373HCID 20068373, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 5.1 parts of 1-(1,2,3,4-tetrahydro-2,2-dimethyl-1-naphthalenyl)-1H-imidazole-5-methanamine and 75 parts of trichloromethane were added 1.2 parts of isocyanatomethane. After stirring for 1 hour, the reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 4-methyl-2-pentanone and 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.9 parts (46.4%) of N-[[1-(1,2,3,4-tetrahydro-2,2-dimethyl-1-naphthalenyl)-1H-imidazol-5-yl]-methyl]-N'-methylurea; mp. 120.1° C. (compound 2.54).

Workup

  1. customthe reaction mixture was evaporated
  2. customThe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from 4-methyl-2-pentanone and 2,2'-oxybispropane
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-a4ba2445eb754239ba7262ed3b51e9ca
Source dataset
uspto-grants-1989_11
Patent number
US04878940

Reaction notes

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