Chlorosuccinimide → HCID 10214919, compound

HRID 2086131Notes

Reaction equation

C([O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]3[C:12](=[C:13]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C(=O)C)[C:14]4=[CH:15][CH:16]=3)[O:11][CH2:10][C:9]=2[CH:26]=1)(=O)C.C1C(=O)N([Cl:34])C(=O)C1>CN(C=O)C>[Cl:34][C:15]1[C:14]2=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=[C:13]2[C:12]2[O:11][CH2:10][C:9]3[CH:26]=[C:5]([OH:4])[CH:6]=[CH:7][C:8]=3[C:17]=2[CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The title compound was prepared by reacting 1-(Acetyloxy)-6H-dibenzo[c,h]chromen-8-yl acetate(360 mg, 1.03 mmol) with NCS (210 mg, 1.57 mmol) and anhydrous DMF (20 ml) according to method B for 2.0 h at room temperature, followed by heating to 100° C. for 1 h. The reaction was concentrated under reduced pressureAnd the solids were dissolved in MeOH (30 ml). NH3 was bubbled in for 0.5 h while acetate removal was monitored by LC-MS. The reaction was concentrated to a dark sludge, dissolved in EtOAc and passed through a silica plug to produce 200 mg (65%) foam. An analytical sample was produced by silica chromatography (1:1 EtOAc:hexanes). mp ˜185° C. dec.; 1H NMR (400 MHz, DMSO-d6) δ 5.23 (2H, s), 6.72 (1H, d, J=2.3 Hz), 6.81 (1H, dd, J=8.6 Hz, 2.6 Hz), 6.92 (1H, dd, J=7.5 Hz, 1.0 Hz), 7.33 (1H, appt), 7.62 (1H, dd, J=8.5 Hz, 1.0 Hz), 7.69 (1H, d, J=8.6 Hz), 7.79 (1H, s), 9.78 (1H, s), 10.11 (1H, s); MS m/z297/399 (Cl pattern) (M−H+).

Workup

concentrationThe reaction was concentrated
dissolutionwere dissolved in MeOH (30 ml)
customNH3 was bubbled in for 0.5 h while acetate removal
concentrationThe reaction was concentrated to a dark sludge
dissolutiondissolved in EtOAc

Sources & evidence

ORD record: ord-e40077617a804da5aa59ac4e7207d265
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723747B2

Reaction notes

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