Methyl Isocyanate → HCID 19003053, compound

HRID 1613464Notes

Reaction equation

HRID 1613464 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][C:7]([OH:11])=[CH:6][C:5]=2[C:4]2[CH2:12][CH2:13][C:14](=[N:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]1=2.N12CCCN=C1CCCCC2.[CH3:34][N:35]=[C:36]=[O:37]>C(Cl)Cl>[CH3:34][NH:35][C:36](=[O:37])[O:11][C:7]1[CH:8]=[CH:9][C:10]2[N:2]([CH3:1])[C:3]3[C:14](=[N:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:13][CH2:12][C:4]=3[C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15288858HCID 15288858, compound

Product 1

HCID 19003053HCID 19003053, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-methyl-3-phenylmethylimino-1,2,3,4-tetrahydrocyclopent[b]indol-7-ol (2.0 g) in CH2Cl2 (40 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.16 g) followed by the dropwise addition of methyl isocyanate (0.39 g) in CH2Cl2 (10 ml). The reaction was monitored via TLC and after 3 hours the solution was concentrated and the precipitate was collected and recrystallized from acetonitrile to give 4-methyl-3-phenylmethylimino-1,2,3,4-tetrahydrocyclopent[b]indol-7-yl methylcarbamate (1.85 grams).

Workup

  1. concentrationthe solution was concentrated
  2. customthe precipitate was collected
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-931266751473400eb0c54fb919aabc68
Source dataset
uspto-grants-1993_03
Patent number
US05192789

Reaction notes

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