HCID 15983581, compound → HCID 46916885, compound

HRID 2358925Notes

Reaction equation

HRID 2358925 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH:11][C:12]([C:14]23[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:22][C:16]([C:24]5[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=5)([CH2:17]4)[CH2:15]2)[CH2:21]3)=[O:13])[CH:5]=[CH:6][C:7]=1[OH:8]>C(OC(=O)C)(=O)C.OS(O)(=O)=O>[C:2]([O:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH:11][C:12]([C:14]23[CH2:21][CH:20]4[CH2:19][CH:18]([CH2:17][C:16]([C:24]5[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=5)([CH2:22]4)[CH2:15]2)[CH2:23]3)=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][C:12](=[O:13])[CH3:14])(=[O:1])[CH3:7]

Participants

4

Reactant 1

HCID 15983581HCID 15983581, compound

Product 1

HCID 46916885HCID 46916885, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Compound 1 (1 g) was dissolved in 10 mL of acetic anhydride with a catalytic amount of 98% H2SO4 and stirred under N2 for 3 days at room temperature. The solution was then concentrated under a vacuum and filtered to give the product Compound 2 (yield=54%), with a melting point of 160-162° C. 1H NMR (500 MHz, CDCl3) δ 1.74 (m, 2H, Admant-H), 1.81-1.88 (m, 8H, Admant-H), 1.93 (s, 2H, Admant-H), 2.26-2.27 (m, 2H, Admant-H), 2.28 (s, 3H, COCH3), 2.31 (s, 3H, COCH3), 2.83-2.85 (t, J=5 Hz, 2H, CH2), 3.50-3.54 (q, 2H, NCH2), 5.69 (s, 1H, NH), 7.01-7.02 (d, J=5 Hz, 1H, Ar—H), 7.07-7.09 (d, d, 1H, H—Ar), 7.13-7.15 (d, J=10 Hz, 1H, Ar—H), 7.30 (s, 4H, Ar—H). 13C NMR (500 MHz, CDCl3) δ 20.6, 20.7, 28.8, 35.0, 35.5, 36.5, 38.3, 40.2, 40.3, 41.7, 42.0, 44.5, 123.5, 124.0, 126.4, 127.0, 128.3, 131.5, 138.0, 140.6, 142.0, 148.4, 168.4, 168.5, 177.5. Mass spectroscopy m/z (relative intensity) 510.24 (M+, 100), 511.24 (38), 512.24 (45).

Workup

  1. concentrationThe solution was then concentrated under a vacuum
  2. filtrationfiltered

Sources & evidence

ORD record
ord-f7c7d8d5ad41443d99d57e0d5c5da241
Source dataset
uspto-grants-2014_04
Patent number
US08685936B2

Reaction notes

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