3-Hydroxybenzaldehyde → HCID 86590217, compound

HRID 413971Notes

Reaction equation

HRID 413971 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])N.[CH3:11][C:12]1[NH:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][C:13]=1[CH2:23][CH2:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH:29]=O.OC1C=[C:37](C=CC=1)[CH:38]=[O:39].ClCCC1N=C(C2C=CC=CC=2)[NH:49][C:50]=1[CH3:51].[C:58]([CH2:60]C(OCC)=O)#[N:59].O=P(Cl)(Cl)Cl.[SH:71][CH2:72]C(OCC)=O>ClCCl.C(OCC)(=O)C>[NH2:59][C:58]1[C:60]2[C:29]([C:28]3[CH:31]=[CH:32][CH:33]=[C:26]([O:25][CH2:24][CH2:23][C:13]4[N:14]=[C:15]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[NH:16][C:12]=4[CH3:11])[CH:27]=3)=[N:49][C:50]([CH3:51])=[N:10][C:8]=2[S:7][C:6]=1[C:72]([O:39][CH2:38][CH3:37])=[S:71]

Participants

9

Reactant 7

HCID 1013-HydroxybenzaldehydeHCID 7764Ethyl cyanoacetateHCID 12185Ethyl ThioglycolateHCID 24813Phosphorus oxychlorideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 22597575HCID 22597575, compoundHCID 22597658HCID 22597658, compound

Product 1

HCID 86590217HCID 86590217, compound

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Cyclization of S-methylisothiourea sulfate (139 mg), 3-{2-[5-methyl-2-phenylimidazol-4-yl]ethoxy}benzaldehyde (496 mg, synthesized from 3-hydroxybenzaldehyde (489 mg) and 4-chloroethyl-5-methyl-2-phenylimidazole (1.03 g) via the procedure described in example 79a) and ethyl cyanoacetate (112 μl), treatment of the product with POCl3 and subsequent reaction with ethyl 2-mercaptoacetate were performed according to the methods described in example 1. The pure title compound was obtained after chromathography on silicagel in dichloromethane/ethyl acetate=10010 (v/v)→70(30 (v/v) as eluent.

Sources & evidence

ORD record
ord-af844466ee394f08a47a228c05971625
Source dataset
uspto-grants-2003_05
Patent number
US06569863B1

Reaction notes

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