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Dimethyl Sulfoxide → 5,10-Dihydro-2-nitro-11H-dibenzo(b,e)(1,4)diazepin-11-one

HRID 895975
Notes
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Reaction equation

HRID 895975 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1Cl.[NH2:15][C:16]1C=C[CH:19]=[CH:18][C:17]=1N.C([N:25]([CH2:28][CH3:29])[CH2:26]C)C.CS(C)=[O:32]>O>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]2[NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:29][C:28]=3[NH:25][C:26](=[O:32])[C:5]=2[CH:6]=1)([O-:12])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 83343Methyl 2-chloro-4-nitrobenzoate

Product 1

HCID 38214715,10-Dihydro-2-nitro-11H-dibenzo(b,e)(1,4)diazepin-11-oneYield 43%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

2-Chloro-4-nitrobenzoic acid methylester (15 g, 69.6 mmol), 1,2-diaminobenzene (69.6 mmol) and triethylamine (9.7 mL, 69.7 mmol) were heated together at 90° C. in DMSO for 4 hr then to 120C for 1hr. After this time, the reaction was diluted with water (50 mL) and a reddish-brown precipitate formed. The solid was filtered off and washed with methanol (2×30 mL) to give the desired product (yield 7.6 g, 43%).

Workup

  1. customa reddish-brown precipitate formed
  2. filtrationThe solid was filtered off
  3. washwashed with methanol (2×30 mL)

Sources & evidence

ORD record
ord-52378cb4019342ba8f4660e5b9c06008
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06919328B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes