Benzoyl isothiocyanate → HCID 86661669, compound

HRID 1261971Notes

Reaction equation

HRID 1261971 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([NH2:14])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[C:15]([N:23]=[C:24]=[S:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([NH:14][C:24]([NH:23][C:15](=[O:22])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[S:25])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 57416054Methyl 1-amino-1H-indole-2-carboxylate

Product 1

HCID 86661669HCID 86661669, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Amino-1H-indole-2-carboxylic acid methyl ester (18.56 g, 0.098 mol) was dissolved in tetrahydrofuran (800 mL). Benzoyl isothiocyanate (13.1 mL, 0.098 mol) was added and the reaction was allowed to stir overnight. The solvent was removed in vacuum and the solid residue was triturated with ether. The solid was collected by filtration to yield the 1-(3-benzoyl-thioureido)-1H-indole-2-carboxylic acid methyl ester (24.27 g, 70%), which was used in the next step without further purification. 1H-NMR (CDCl3) δ 12.81 (br s, 1H), 9.29 (br s, 1H), 7.95 (d, J=7.2 Hz, 2H), 7.68 (m, 2H), 7.57 (m, 2H), 7.42 (m, 2H), 7.38 (s, 1H), 7.24 (m, 1H), 3.89 (s, 3H).

Workup

  1. customThe solvent was removed in vacuum
  2. customthe solid residue was triturated with ether
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-5884a61420f84d71aa9860ba6841e753
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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