N-(4-chlorophenyl)benzene-1,2-diamine → HCID 70978917, compound

HRID 1485407Notes

Reaction equation

HRID 1485407 reaction equation
Cl[C:2]([C:4]1([C:12](Cl)=[O:13])[CH2:6][CH:5]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:3].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[C:24]([NH2:29])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:18][CH:17]=1>ClCCl.C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:2](=[O:3])[C:4]3([CH2:6][CH:5]3[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12](=[O:13])[NH:29][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]2=3)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 522323N-(4-chlorophenyl)benzene-1,2-diamineHCID 86718496HCID 86718496, compound

Product 1

HCID 70978917HCID 70978917, compoundYield 15.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2,2-bis(chlorocarbonyl)cyclopropanecarboxylate (2 g, crude product from last step) in dichloromethane (10 mL) was added dropwise to a solution of N1-(4-chlorophenyl)benzene-1,2-diamine (2.2 g, 10 mmol) in toluene (50 mL) and the resulting mixture was heated to 100° C. for 48 h. The solvent was evaporated and the residue was purified by CombiFlash (PE:EA=5:1) to obtained ethyl 1-(4-chlorophenyl)-2,4-dioxo-1,2,4,5-tetrahydrospiro[benzo[b][1,4]diazepine-3,1′-cyclopropane]-2′-carboxylate (500 mg, 13%). LRMS (M+H)+: 384 m/z. 1H NMR (300 MHz, CDCl3): δ 1.07-1.12 (t, J=7.2 Hz, 3H), 1.72-1.81 (m, 1H), 2.16-2.18 (m, 1H), 2.41-2.43 (br, 1H), 3.92-4.00 (m, 2H), 7.20-7.25 (m, 1H), 7.42-7.49 (m, 4H), 7.52-7.65 (m, 3H), 8.06-8.08 (m, 1H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by CombiFlash (PE:EA=5:1)

Sources & evidence

ORD record
ord-e66a3b6442e14c69b9ee00c514b71ce5
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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