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

HRID 1365079Notes

Reaction equation

HRID 1365079 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(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

4

Reactant 2

HCID 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 triethylammine (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-6,11-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-de8f73a167f548f7a97fe69acee54284
Source dataset
uspto-grants-2011_02
Patent number
US07888506B2

Reaction notes

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