Sodium hydride → N-(4-methyl-2-thiazolyl)-N-(2-dimethylaminoethyl)acetamide

HRID 1733292Notes

Reaction equation

HRID 1733292 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[H-].[Na+].Cl.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17]Cl>CN(C=O)C>[CH3:10][C:8]1[N:9]=[C:5]([N:4]([CH2:17][CH2:16][N:15]([CH3:19])[CH3:14])[C:1](=[O:3])[CH3:2])[S:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 280907N-(4-Methylthiazol-2-yl)acetamideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 12791196N-(4-methyl-2-thiazolyl)-N-(2-dimethylaminoethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction is run under a nitrogen atmosphere. To a stirred solution of 31.2 g. (0.20 mole) of 2-acetamido-4-methylthiazole in 300 ml. of DMF is added 9.6 g. (0.20 mole) of a 50% suspension of sodium hydride in mineral oil. The reaction is stirred for 1/2 hour as the temperature spontaneously rises to 50° C. The reaction is cooled to 35° to 40° C. and a further 12.0 g. (0.25 mole) of sodium hydride suspension added followed by 36.0 g. (0.25 mole) of 2-dimethylaminoethyl chloride HCl, added portionwise for 10 to 15 minutes. The mixture is stirred at room temperature for about 1 hour and then at steam bath temperature for 20 hours. The tan mixture is cooled to ambient temperature and filtered to remove salts. The filtrate is concentrated under reduced pressure at steam bath temperature. This gives 46.4 g. of crude product as a brown oil (containing mineral oil (10.8 g.).

Workup

  1. customspontaneously rises to 50° C
  2. temperatureThe reaction is cooled to 35° to 40° C.
  3. stirringThe mixture is stirred at room temperature for about 1 hour
  4. waitat steam bath temperature for 20 hours
  5. filtrationfiltered
  6. customto remove salts
  7. concentrationThe filtrate is concentrated under reduced pressure at steam bath temperature
  8. additionof crude product as a brown oil (containing mineral oil (10.8 g.)

Sources & evidence

ORD record
ord-79cad6fa78b048ad966418036c55b961
Source dataset
uspto-grants-1980_12
Patent number
US04241072

Reaction notes

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