Benzenecarbothioamide, 3-chloro- → HCID 11354397, compound

HRID 1455650Notes

Reaction equation

Br[CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[CH:22]=[C:23]([C:31]([CH3:37])([S:33]([CH3:36])(=[O:35])=[O:34])[CH3:32])[CH:24]=[C:25]3[C:30]=2[N:29]=[CH:28][CH:27]=[CH:26]3)[CH:16]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.[Cl:38][C:39]1[CH:40]=[C:41]([C:45](=[S:47])[NH2:46])[CH:42]=[CH:43][CH:44]=1>CN(C=O)C.O.C([O-])(O)=O.[Na+].CCOCC>[Cl:38][C:39]1[CH:40]=[C:41]([C:45]2[S:47][C:2]([C:15]3[CH:16]=[C:17]([C:21]4[CH:22]=[C:23]([C:31]([CH3:37])([S:33]([CH3:36])(=[O:35])=[O:34])[CH3:32])[CH:24]=[C:25]5[C:30]=4[N:29]=[CH:28][CH:27]=[CH:26]5)[CH:18]=[CH:19][CH:20]=3)=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=3)[N:46]=2)[CH:42]=[CH:43][CH:44]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the alpha-bromoketone from step 4 (1.0 eq) in DMF (0.1M) was added 3-chlorobenzenecarbothioamide (1.0 eq). The mixture was heated at 40-120° C. for 1-3 h, cooled, diluted with water, saturated NaHCO3 solution and ether. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (Hexane:EtOAc) to afforded the title compound.

Workup

temperaturecooled
washThe organic extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography (Hexane:EtOAc)

Sources & evidence

ORD record: ord-12506ed09b6344cf9a28651bb28f1dc2
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482456B2

Reaction notes

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