4-Chloroaniline → HCID 78322061, compound

HRID 1775652Notes

Reaction equation

HRID 1775652 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:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)=[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:50][C:4]1[CH:5]=[CH:6][C:1]([N:7]2[C:36](=[O:38])[C:25]3[S:26][CH:27]=[C:28]([C:29]4[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=4)[C:24]=3[N:23]=[CH:12]2)=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 31214Ethyl orthoformateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-oneHCID 86729806HCID 86729806, compound

Product 1

HCID 78322061HCID 78322061, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(m -tolyl)thiophene-2-carboxylate (80 mg, 0.32 mmol), triethyl orthoformate (0.7 ml), 4-chloroaniline (76.8 mg, 0.6 mmol), and acetic acid (0.1 ml) were used to give 85.1 mg (0.23 mmol, 72.1% yield) of the title compound.

Sources & evidence

ORD record
ord-556110a84567458d9d87b563d9385393
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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