Sodium ethoxide → HCID 22478414, compound

HRID 2182206Notes

Reaction equation

HRID 2182206 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1.[Na].[SH:22][C:23]1[N:24]([CH3:28])[CH:25]=[CH:26][N:27]=1.SC1N(C)C=CN=1.[O-]CC.[Na+]>C(O)C>[CH3:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[NH:13][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][S:22][C:23]3[N:24]([CH3:28])[CH:25]=[CH:26][N:27]=3)[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 224784026-Bromomethyl-4-(3-methylanilino)quinazolineHCID 178480602HCID 178480602, compoundHCID 178480605HCID 178480605, compound

Product 1

HCID 22478414HCID 22478414, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using an analogous procedure to that described in Example 34, 6-bromomethyl-4-(3-methylanilino)quinazoline was reacted with 2-mercapto-1-methylimidazole sodium salt [prepared by the reaction of 2-mercapto-1-methylimidazole and sodium ethoxide in ethanol] to give 4-(3-methylanilino)-6-(N-methylimidazol-2-ylthiomethyl)quinazoline in 65% yield, m.p. 137-139° C.;

Sources & evidence

ORD record
ord-8e817b0a01634fab86311f9de3c98f7a
Source dataset
uspto-grants-2005_05
Patent number
US06897214B2

Reaction notes

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