(4-Aminophenoxy)benzene → HCID 22112879, compound

HRID 564792Notes

Reaction equation

HRID 564792 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[O:12]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(O)C>[ClH:1].[CH3:11][C:10]1[C:3]2[C:2]([NH:23][C:22]3[CH:21]=[CH:20][C:19]([O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:25][CH:24]=3)=[N:7][CH:6]=[N:5][C:4]=2[S:8][CH:9]=1

Participants

4

Reactant 2

HCID 8764(4-Aminophenoxy)benzeneHCID 2902254-Chloro-5-methylthieno[2,3-d]pyrimidine

Product 1

HCID 22112879HCID 22112879, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chloro-5-methylthieno[2,3-d]pyrimidine (0.185 g, 1.00 mmol) and 4-phenoxyaniline (0.210 g, 1.1 mmol) were reacted in 2-propanol (6 ml) for 17 hours according to Procedure A. The product was obtained as a pale grey solid (0.297 g, 80%), m.p. 218-221° C.; (Found: C, 61.61; H, 4.33, N, 11.25. C19H15N3OS.HCl requires: C, 61.70; H, 4.36; N, 11.36%); δH [2H6]-DMSO 8.60 (1H, br s, NH), 8.49 (1H, s, 2-H), 7.68 (2H, d, J 9, 2′-H, 6′-H), 7.33-7.48 (3H, m, 6-H, 3″-H, 5″-H), 7.17 (1H, t, J 9, 4″-H), 7.00-7.10 (4H, m, 3′-H, 5′-H, 2″-H, 6″-H), 2.75 (3H, s, 5-CH3); m/z 333 (M+).

Sources & evidence

ORD record
ord-62df109e8bb64b21b73c635b662bb3d0
Source dataset
uspto-grants-2001_01
Patent number
US06169091A

Reaction notes

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