2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → HCID 70274702, compound

HRID 867950Notes

Reaction equation

HRID 867950 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[N:7]=[C:8]([CH2:11][N:12]([CH3:14])[CH3:13])[S:9][CH:10]=1.[O:15]([C:22](OC1C=CC=CC=1)=[CH:23][N+:24]([O-:26])=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[CH3:13][N:12]([CH2:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][S:4][CH2:3][CH2:2][NH:1][C:22]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:23][N+:24]([O-:26])=[O:25])[N:7]=1)[CH3:14]

Participants

4

Reactant 2

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 12696039HCID 12696039, compound

Product 1

HCID 70274702HCID 70274702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure of Example 2, a solution of 1.65 (6.8 mmol) of 95% pure 4-[[(2-aminoethyl)thio]methyl]-N,N-dimethyl-2-thiazolemethanamine and 1.8 g (7.0 mmol) of 1,1-diphenoxy-2-nitroethene dissolved in 25 ml of methylene chloride was stirred at room temperature for about two hours to provide N-[2-[[[2-[(dimethylamino)methyl]-4-thiazolyl]methyl]thio]ethyl]-2-nitro-1-phenoxy-1-etheneamine in situ. This compound was reacted with gaseous monomethylamine to provide 0.8 g of nizatidine. Yield 35.5%.

Sources & evidence

ORD record
ord-0a52849ac0eb4b98a07081508b63b5ac
Source dataset
uspto-grants-1988_10
Patent number
US04777260

Reaction notes

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