Methanol → 9-Ethyl-3-isocyanatocarbazole

HRID 2413673

Reaction equation

HRID 2413673 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:15][CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C(N(CC)CC)C.[CH3:24][OH:25].C1(N=C=NC2CCCCC2)CCCCC1>C(=S)=S>[CH2:15]([N:6]1[C:5]2[CH:4]=[CH:3][C:2]([N:1]=[C:24]=[O:25])=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH3:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 85883-Amino-9-ethylcarbazoleHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 201550999-Ethyl-3-isocyanatocarbazole

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

38.6 g of 3-amino-9-ethylcarbazole and 27.9 ml of triethylamine were added to 300 ml of methanol, and, while cooling with ice, 15.2 g of carbon disulfide was added dropwise thereto. After conducting reaction at room temperature for 3 hours, 41.3 g of dicyclohexylcarbodiimide was added thereto, followed by reacting at room temperature for 4 hours. Crystals thus precipitated were collected by filtration, heat-refluxed in 500 ml of ethyl acetate, and cooled to precipitate and then filter off solids. The filtrate was concentrated to obtain the desired product (29 g).

Workup

  1. additionwas added dropwise
  2. customreaction at room temperature for 3 hours
  3. customCrystals thus precipitated
  4. filtrationwere collected by filtration
  5. temperatureheat-refluxed in 500 ml of ethyl acetate
  6. temperaturecooled
  7. customto precipitate
  8. filtrationfilter off solids
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9e5e9b55f683429fa89f2bf67ac707ea
Source dataset
uspto-grants-1988_01
Patent number
US04719174

Linked notes

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