Iodoethane → HCID 178466918, compound

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[N:9]=[CH:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[S:21][C:22]4[CH2:28][CH2:27][CH2:26][CH:25]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:23]=4[N:24]=3)=[CH:15][C:14]=2[OH:35])[CH:12]=1.[I:36][CH2:37][CH3:38].[C:39](#N)[CH3:40]>>[I-:36].[CH2:39]([O:35][C:14]1[CH:15]=[C:16]([NH:19][C:20]2[S:21][C:22]3[CH2:28][CH2:27][CH2:26][CH:25]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:23]=3[N:24]=2)[CH:17]=[CH:18][C:13]=1[N:11]1[CH:12]=[C:8]([CH3:7])[N+:9]([CH2:37][CH3:38])=[CH:10]1)[CH3:40]

Participants

Reactant 4

HCID 6340Iodoethane

HCID 6342Acetonitrile

HCID 11430Potassium Carbonate

HCID 44193857HCID 44193857, compound

Product 1

HCID 178466918HCID 178466918, compoundYield 45%

Procedure

Potassium carbonate (41.5 mg, 0.3 mmol) was added to a solution of 2-(4-methyl-imidazol-1-yl)-5-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-ylamino)-phenol (60.4 mg, 0.15 mmol), iodoethane (15 uL, 0.18 mmol) in acetonitrile (1.5 mL). The reaction was refluxed over night and the solvent was removed under reduced pressure. The residue was purified on silica gel using dichloromethane/methanol/concentrated aqueous ammonia (9:1:0.1 v/v/v) as eluent to yield the title compound (29 mg, 45%) as a beige solid. MS ISP (m/e): 459.4 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.39 (s, 1H), 9.31 (s, 1H), 7.83 (s, 1H), 7.67 (s, 1H), 7.34 (d, 1H), 7.29 (t, 2H), 7.14-7.21 (m, 3H), 6.82 (d, 1H), 4.18 (q, 2H), 3.99 (m, 1H), 3.59 (dq, 1H), 3.50 (dq, 1H), 2.64-2.82 (m, 2H), 2.34 (s, 3H), 2.17 (m, 1H), 1.90 (m, 1H), 1.76 (m, 2H), 1.43 (t, 3H), 1.14 (t, 3H).