4-Chloroaniline → HCID 78322372, compound

HRID 1775660Notes

Reaction equation

HRID 1775660 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.NC1C(C2C=CC(OC)=CC=2)=CSC=1C([O:39][CH3:40])=O.C(OCC)(OCC)OCC.[Cl:51]C1C=CC(N)=CC=1>C(O)(=O)C>[Cl:51][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[CH:18]=[CH:19][C:20]([O:39][CH3:40])=[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 2759760HCID 2759760, compoundHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78322372HCID 78322372, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(4-methoxyphenyl)thiophene-2-carboxylate (80 mg, 0.3 mmol), triethyl orthoformate (0.66 ml), 4-chloroaniline (71.2 mg, 0.56 mmol), and acetic acid (0.08 ml) were used to give 96.2 mg (0.26 mmol, 86.9% yield) of the title compound.

Sources & evidence

ORD record
ord-af9a57f473f848768c8281d531d1d933
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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