Chloroform methanol ammonia → HCID 178465563, compound

HRID 386672Notes

Reaction equation

HRID 386672 reaction equation
[ClH:1].Cl.[N:3]1([C:8]2[CH:9]=[C:10]([C:14]3[O:15][C:16]4[CH:32]=[CH:31][C:30]([NH:33][C:34](=[NH:36])[CH3:35])=[CH:29][C:17]=4[C:18](=[O:28])[C:19]=3[O:20]CC3C=CC=CC=3)[CH:11]=[CH:12][CH:13]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.C(Cl)(Cl)[Cl:38].CO.N>>[ClH:38].[ClH:1].[N:3]1([C:8]2[CH:9]=[C:10]([C:14]3[O:15][C:16]4[CH:32]=[CH:31][C:30]([NH:33][C:34](=[NH:36])[CH3:35])=[CH:29][C:17]=4[C:18](=[O:28])[C:19]=3[OH:20])[CH:11]=[CH:12][CH:13]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

3

Reactant 2

HCID 21866414Chloroform methanol ammoniaHCID 178465562HCID 178465562, compound

Product 1

HCID 178465563HCID 178465563, compoundYield 90%

Procedure

Prepared analogously to Example 5, starting from 2-[(3-(imidazol-1-yl)-phenyl]-3-benzyloxy-6-[(1-iminoethyl)amino]-4H-1-benzopyran-4-one dihydrochloride. Yield: 90%; m.p.: 281.0-281.5° C. TLC (80/20/2 Chloroform/Methanol/Ammonia) Rf: 0.32; Elem. anal.: C20H16N4O3.2HCl, Theory: C, 55.44; H, 4.19; N, 12.93. Found: C, 53.05; H, 4.34; N, 12.18. 1H-NMR (d6-DMSO): 11.83 (s broad, 1H), 10.30 (s, 1H), 9.75 (m, 2H), 8.73 (s broad, 1H), 8.46 (m, 2H), 8.38 (m, 1H), 8.07-7.75 (m, 6H), 2.41 (s, 3H).

Workup

  1. customPrepared analogously to Example 5

Sources & evidence

ORD record
ord-c7b7fdd592424424ad42fcd2bd44e8f7
Source dataset
uspto-grants-2013_02
Patent number
US08372866B2

Reaction notes

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