Thionyl Chloride → HCID 178522615, compound

HRID 518728Notes

Reaction equation

[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:23][C:12]=3[N:13]\2[C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20](O)=[O:21])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:38])=O>C(Cl)Cl>[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:23][C:12]=3[N:13]\2[C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([Cl:38])=[O:21])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. suspension of cis-4-((E)-2-(4-fluorobenzoylimino)-6-(morpholinomethyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylic acid (0.5 g, 1.041 mmol) in DCM (10.41 mL) was added thionyl chloride (0.380 mL, 5.20 mmol). The suspension was stirred for 30 minutes at 0° C. The reaction was concentrated, resuspended in ACN (5 mL), and reconcentrated to generate cis-4-((E)-2-(4-fluorobenzoylimino)-6-(morpholinomethyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarbonyl chloride (0.50 g, 96% yield) as a white powder.

Workup

concentrationThe reaction was concentrated

Sources & evidence

ORD record: ord-c65c6a5dcc3d4dc48a1833ba30bc724a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115127B2

Reaction notes

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