Benzoyl isothiocyanate → HCID 11666512, compound

HRID 536097Notes

Reaction equation

HRID 536097 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][NH:11][C:12]2[CH:16]=[CH:15][NH:14][C:13]=2[C:17]([O:19]CC)=O)=[CH:2]1.C([N:30]=[C:31]=[S:32])(=O)C1C=CC=CC=1>CO.C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][N:11]2[C:12]3[CH:16]=[CH:15][NH:14][C:13]=3[C:17](=[O:19])[NH:30][C:31]2=[S:32])=[CH:2]1

Participants

5

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 67068493HCID 67068493, compound

Product 1

HCID 11666512HCID 11666512, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

A crude mixture of ethyl 3-[(1H-indol-3-ylmethyl)amino]-1H-pyrrole-2-carboxylate (max 0.49 mmol) was added to CH2Cl2 (5 mL). A few drops of methanol were added to increase solubility. Benzoylisothiocyanate (0.072 g, 0.53 mmol) was added and the mixture was stirred at r.t. for 1 h. The mixture was concentrated in vacuo. Ammonia (7N in methanol, 3 mL) was added and the mixture was heated at 80° C. for 2 h. The mixture was concentrated and purified by preparative HPLC, obtaining the title compound (0.030 g, 21%) as a solid.

Workup

  1. temperatureto increase solubility
  2. concentrationThe mixture was concentrated in vacuo
  3. additionAmmonia (7N in methanol, 3 mL) was added
  4. temperaturethe mixture was heated at 80° C. for 2 h
  5. concentrationThe mixture was concentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-cca8654dee0d454eb78875b3d981d762
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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