Triethylamine → 4,4-Dimethyl-4H-5-oxa-1,3-dithia-6,11-diaza-cyclopenta[a]anthracen-2-one

HRID 887969Notes

Reaction equation

HRID 887969 reaction equation
O[C:2]([C:5]1[S:9][C:8](=[O:10])[S:7][C:6]=1[C:11]1[C:12](=[O:21])[NH:13][C:14]2[C:19]([N:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)([CH3:4])[CH3:3].C(OC(Cl)=O)C1C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:4][C:2]1([CH3:3])[O:21][C:12]2[C:11](=[N:20][C:19]3[C:14]([N:13]=2)=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:6]2[S:7][C:8](=[O:10])[S:9][C:5]1=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 866217983-(5-(2-hydroxypropan-2-yl)-2-oxo-1,3-dithiol-4-yl)quinoxalin-2(1H)-one

Product 1

HCID 251667594,4-Dimethyl-4H-5-oxa-1,3-dithia-6,11-diaza-cyclopenta[a]anthracen-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(5-(2-Hydroxypropan-2-yl)-2-oxo-1,3-dithiol-4-yl)quinoxalin-2(1H)-one (6) (130 mg, 0.405 mmol) was partially dissolved in CH2Cl2 (10 mL). Benzylchloroformate (125 μL, 0.81 mmol) and triethylamine (120 μL) were added and the resulting yellow solution was stirred overnight. The volume of the solution was reduced to ca. 3 mL and it was purified by chromatography (silica gel, CH2Cl2) to give pure 4,4-dimethyl-4H-5-oxa-1,3-dithia-6,1,1-diaza-cyclopenta[a]anthracen-2-one (7). Yield: 82 mg (70%).

Workup

  1. customwas purified by chromatography (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-16b589a02f0e46bf96f7510adc56f011
Source dataset
uspto-grants-2012_08
Patent number
US08247551B2

Reaction notes

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