Carbon Disulfide → HCID 59485731, compound

HRID 1972222Notes

Reaction equation

[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[CH2:15][NH2:16])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:29](=S)=[S:30].CCN(C(C)C)C(C)C>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:25])[F:26])[CH:18]=4)[CH2:15][NH:16][C:29]3=[S:30])=[CH:9][CH:8]=2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N1-(4-(4-chlorophenoxy)phenyl)-1-(3-(trifluoromethyl)phenyl)ethane-1,2-diamine (127 mg, 0.312 mmol) in EtOH (2.0 mL) are added CS2 (188 μL, 3.12 mmol) and iPr2NEt (272 μL, 1.56 mmol). The reaction mixture is heated at 80° C. overnight before removal of the solvent. The residue is purified by silica gel chromatography (0˜40% EtOAc/Hexanes) to provide the title compound (95.9 mg, 69% yield) as a white solid product; HPLC-MS calculated for C22H16ClF3N2OS (M+H+) 449.1, found 449.1.

Workup

customThe residue is purified by silica gel chromatography (0˜40% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-7b85b0a42077464eb4d8454fc8a1c8ce
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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