Aniline → HCID 178501725, compound

HRID 411245Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]([O-])=O.[Na+].[Cl:12][C:13]1[S:14][C:15]([CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[CH:16][C:17]=1[C:18](=[O:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21]>Cl.O.N1C=CC=CC=1>[Cl:12][C:13]1[S:14][C:15]([CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[CH:16][C:17]=1[C:18](=[O:24])/[C:19](=[N:8]/[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)/[C:20]([O:22][CH3:23])=[O:21]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of aniline (2.52 mL) in 6M HCl (15 mL) is added dropwise a solution of NaNO2 (2.44 g) in water (8 mL) at -10° C. The solution stirs at 0° C. for 1 h and is poured into a solution of methyl 3-(2-chloro-5-(4-morpholinylmethyl)-3-thienyl)-3-oxopropanoate (Preparation 64, 3.50 g) in pyridine (15 mL) and water (8 mL) with vigorous stirring at −10° C. The solution stirs at 0° C. for 60 min and is diluted with cold water (150 mL). The aqueous layer is extracted with EtOAc (3×150 mL). The organic layers are combined, dried over MgSO4, filtered, and concentrated in vacuo. The crude red liquid (2.93 g) is utilized without any further purification. Physical characteristics: IR (liq.) 1737, 1675, 1529, 1455, 1437, 1330, 1306, 1263, 1239, 1218, 1201, 1168, 1144, 1117, 755 cm−1; MS (FAB) m/z 422 (MH+); HRMS (FAB) m/z 422.0935 (C19H20ClN3O4S+H).

Workup

waitThe solution stirs at 0° C. for 60 min
extractionThe aqueous layer is extracted with EtOAc (3×150 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude red liquid (2.93 g) is utilized without any further purification

Sources & evidence

ORD record: ord-ac8a2d778c9449298ff787d6cfbfb759
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559145B2

Reaction notes

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