Thiourea → 4-(2,4,6-Trimethylphenyl)-1,3-thiazol-2-amine

HRID 1531587Notes

Reaction equation

HRID 1531587 reaction equation
BrCC(CBr)=O.BrC[CH2:9][C:10]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20])=O.[NH2:21][C:22]([NH2:24])=[S:23]>CO>[NH2:24][C:22]1[S:23][CH:9]=[C:10]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[N:21]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 1317224202,4,6-Trimethylphenyl bromoethyl ketone bromomethylketone

Product 1

HCID 6127164-(2,4,6-Trimethylphenyl)-1,3-thiazol-2-amineYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 80 g of 2,4,6-trimethylphenyl bromoethyl ketone bromomethylketone and 35 g of thiourea in 250 ml of methanol is refluxed for 3 hours. After cooling the reaction mixture, the precipitate is filtered off and washed abundantly with diethyl ether. After concentration of the filtrate to a third of the initial volume, a second bath of crystals is recovered. Yield: 70%. m.p.=138 168° C. The hydrobromide prepared by the action of HBr in ethanol melts at 295° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe precipitate is filtered off
  3. washwashed abundantly with diethyl ether
  4. customAfter concentration of the filtrate to a third of the initial volume, a second bath of crystals is recovered
  5. customm.p.=138 168° C
  6. customThe hydrobromide prepared by the action of HBr in ethanol melts at 295° C.

Sources & evidence

ORD record
ord-6555d9c4c3a845869a8718b9be68d432
Source dataset
uspto-grants-2001_03
Patent number
USRE037094E1

Reaction notes

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