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1-Hydroxybenzotriazole → 7-Nitro-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

HRID 1851393
Notes
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Reaction equation

HRID 1851393 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([OH:15])=O)=[CH:9]2)([O-:3])=[O:2].N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[C:39]([S:58][CH2:59][CH2:60][NH2:61])([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C)C=O.O.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([NH:61][CH2:60][CH2:59][S:58][C:39]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:15])=[CH:9]2)([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 814097-nitro-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochloride

Product 1

HCID 579017857-Nitro-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamideYield 95.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 7-nitro-1H-indole-2-carboxylic acid (4.4 g), 1H-1,2,3-benzotriazol-1-ol (3.8 g), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (4.8 g), 2-(tritylthio)ethylamine hydrochloride (7.4 g) and triethylamine (3.5 mL) in N,N-dimethylformamide (50 mL) was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was crystallized from diethyl ether-hexane to give the title compound (10.1 g, yield 95%) as yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe obtained residue was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-029a7886a5fd49319f4a4a6815dc0907
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957070B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes