Methyl Isocyanate → HCID 19003056, compound

HRID 1613474Notes

Reaction equation

HRID 1613474 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]#[CH: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][CH2:16][C:17]#[CH: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 19003106HCID 19003106, compound

Product 1

HCID 19003056HCID 19003056, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-methyl-3-(2-propynyl)imino-1,2,3,4-tetrahydrocyclopent[b]indol-7-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-(2-propynyl)imino-1,2,3,4-tetrahydrocyclopent[b]indol-7-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-b6184e3cdf2d444aa44198c8a5f7f1b2
Source dataset
uspto-grants-1993_03
Patent number
US05192789

Reaction notes

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