N,N-Dimethylaminothioacetamide hydrochloride → 2-(Dimethylaminomethyl)-4-(phthalimido-1-butyl)thiazole

HRID 354609Notes

Reaction equation

HRID 354609 reaction equation
Cl.[CH3:2][N:3]([CH2:5][C:6]([NH2:8])=[S:7])[CH3:4].[C:9]1(=[O:27])[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([CH2:20]Br)=O)[C:12](=[O:22])[C:11]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:10]12>C(O)C>[CH3:2][N:3]([CH2:5][C:6]1[S:7][CH:20]=[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][N:13]2[C:12](=[O:22])[C:11]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:10]3[C:9]2=[O:27])[N:8]=1)[CH3:4]

Participants

4

Reactant 2

HCID 13121932N,N-Dimethylaminothioacetamide hydrochlorideHCID 14506404Bromomethyl 4-phthalimidobutyl ketone

Product 1

HCID 150534862-(Dimethylaminomethyl)-4-(phthalimido-1-butyl)thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure of Example 1, a stirred solution containing 3.2 g. of dimethylaminothioacetamide hydrochloride, and 6.48 g of bromomethyl 4-phthalimidobutyl ketone [prepared by the procedure of Chem. Listy., 49, 1385 (1955); C.A., 50, 5573c (1956)]; in 50 ml. of ethanol was heated at refluxing temperature for about 5 hours and was then cooled. Volatile constituents were removed by evaporation in vacuo leaving 2-(dimethylaminomethyl)-4-(phthalimido-1-butyl)thiazole as a semi-solid residue. The compound was utilized without further purification.

Workup

  1. additiona stirred solution containing 3.2 g
  2. temperatureat refluxing temperature for about 5 hours
  3. temperaturewas then cooled
  4. customVolatile constituents were removed by evaporation in vacuo

Sources & evidence

ORD record
ord-47fca0e2766741edaed4c1c88dfb0849
Source dataset
uspto-grants-1983_03
Patent number
US04375547

Reaction notes

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