4-Chloroaniline → HCID 78322376, compound

HRID 1775666Notes

Reaction equation

HRID 1775666 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N[C:24]1[C:28]([C:29]2C3C(=CC=CC=3)C=CC=2)=CS[C:25]=1C(OC)=O.C(OCC)(OCC)OCC.[Cl:53]C1C=CC(N)=CC=1>C(O)(=O)C>[Cl:53][C:4]1[CH:5]=[CH:6][C:1]([N:7]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[C:18]5[C:19](=[CH:25][CH:24]=[CH:28][CH:29]=5)[CH:20]=[CH:21][CH:22]=4)[C:10]=3[N:9]=[CH:8]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 86729811HCID 86729811, compound

Product 1

HCID 78322376HCID 78322376, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(naphthalen-1-yl)thiophene-2-carboxylate (43.8 mg, 0.15 mmol), triethyl orthoformate (0.32 ml), 4-chloroaniline (44.3 mg, 0.4 mmol), and acetic acid (0.04 ml) were used to give 27 mg (0.07 mmol, 46.3% yield) of the title compound.

Sources & evidence

ORD record
ord-db9b0b5c8cae4096b91326de9668cef1
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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