Methyl Isocyanate → N-Methyl-N'-(4,4-dimethyl-1,2,3,4-tetrahydro-1,3-dioxo-7-isoquinolinyl)-urea

HRID 621417

Reaction equation

HRID 621417 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])([CH3:14])[C:7](=[O:13])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[CH3:16][N:17]=[C:18]=[O:19]>C(Cl)Cl>[CH3:16][NH:17][C:18]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])([CH3:14])[C:7](=[O:13])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1)=[O:19]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 135581517-amino-4,4-dimethylisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 10445362N-Methyl-N'-(4,4-dimethyl-1,2,3,4-tetrahydro-1,3-dioxo-7-isoquinolinyl)-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

3 g. (14.7 mMole) 7-amino-4,4-dimethylisoquinoline-1,3-dione were dissolved in 100 ml. methylene chloride, mixed with 5 ml. methyl isocyanate, while cooling, and then further stirred for 2 hours at 25° C. Subsequently, the reaction mixture was evaporated, cooled, filtered off with suction and recrystallised from methanol. Yield: 3.7 g. (96.4% of theory); m.p. 257°-258° C.

Workup

  1. customSubsequently, the reaction mixture was evaporated
  2. temperaturecooled
  3. filtrationfiltered off with suction
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-ee1c2ab484464526bb4d5008061dde8a
Source dataset
uspto-grants-1989_04
Patent number
US04824835

Linked notes

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