4-Chloroaniline → HCID 78321441, compound

HRID 1775642Notes

Reaction equation

HRID 1775642 reaction equation
[C:1]1([N:7]2[C:12](=O)C3SC=C(C4C=CC=CC=4)C=3N=C2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:23][C:24]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])=[CH:27][S:26][C:25]=1[C:36]([O:38]C)=O.C(OCC)(OCC)OCC.[Cl:50]C1C=CC(N)=CC=1>C(O)(=O)C>[Cl:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:28]1[C:24]2[N:23]=[CH:12][N:7]([C:1]3[CH:6]=[CH:5][C:4]([Cl:50])=[CH:3][CH:2]=3)[C:36](=[O:38])[C:25]=2[S:26][CH:27]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 31214Ethyl orthoformateHCID 53335888HCID 53335888, compoundHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78321441HCID 78321441, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(2-chlorophenyl)thiophene-2-carboxylate (100 mg, 0.373 mmol), triethyl orthoformate (2 ml), 4-chloroaniline (88.5 mg, 0.70 mmol), and acetic acid (0.1 ml) were used to give 31.3 mg (0.084 mmol, 23% yield) of the title compound.

Sources & evidence

ORD record
ord-8d177e2e11cb4eefbdf7e5c55cff13e1
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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