Methyl Isocyanate → HCID 19902126, compound

HRID 2372789Notes

Reaction equation

HRID 2372789 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][C:16]#[C:17][CH3:18])[C:3]1=2.N12CCCN=C1CCCCC2.[CH3:30][N:31]=[C:32]=[O:33]>C(Cl)Cl>[CH3:30][NH:31][C:32](=[O:33])[O:11][C:7]1[CH:8]=[CH:9][C:10]2[N:2]([CH3:1])[C:3]3[C:14](=[N:15][C:16]#[C:17][CH3:18])[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 19902133HCID 19902133, compound

Product 1

HCID 19902126HCID 19902126, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-methyl-3-propynylimino-1,2,3,4-tetrahydrocyclopent[b]indol7-ol (3.4 g) in CH2Cl2 (15.0 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (326 mg) followed by the dropwise addition of methyl isocyanate (0.8 g) in CH2Cl2 (5.0 ml). The reaction was monitored via TLC and after 1.0 hour, the solution was concentrated and the crude product was purified via flash chromatography eluting with hexane/acetone (2:1). The product which precipitated out of the pure fractions was collected to give 4-methyl-3-propynylimino-1,2,3,4-tetrahydrocyclopent[b]indol7-yl methylcarbamate (1.2 grams) and the fractions were concentrated to give an additional 0.9 gram.

Workup

  1. concentrationthe solution was concentrated
  2. customthe crude product was purified via flash chromatography
  3. washeluting with hexane/acetone (2:1)
  4. customThe product which precipitated out of the pure fractions
  5. customwas collected

Sources & evidence

ORD record
ord-2328575b342b420e81cab050e2f2f298
Source dataset
uspto-grants-1992_03
Patent number
US05100891

Reaction notes

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