Hydrochloric Acid → 4-(Phenoxymethyl)-1,3-thiazol-2-amine

HRID 2218529Notes

Reaction equation

HRID 2218529 reaction equation
[O:1]([CH2:8][C:9]1[N:10]=[C:11]([NH:14]C(=O)C)[S:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[O:1]([CH2:8][C:9]1[N:10]=[C:11]([NH2:14])[S:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2940526N-[4-(phenoxymethyl)-1,3-thiazol-2-yl]acetamide

Product 1

HCID 20500284-(Phenoxymethyl)-1,3-thiazol-2-amineYield 106.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(4-phenoxymethyl-thiazol-2-yl)-acetamide (40 mg, 0.16 mmol) in THF (2 ml) was added 6N HCl (2 ml). The reaction was heated at 60° C. for 3 hours following by stirring at room temperature overnight and then heated at 60° C. for additional 3 hours. The solution was concentrated to afford 4-phenoxymethyl-thiazol-2-ylamine (HCl salt) as a brown viscous oil (35 mg, 90% ). LC/MS m/z 207.09 (M+1)+; HPLC Rt: 1.137 min

Workup

  1. temperatureheated at 60° C. for additional 3 hours
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-94072ca87f8e4c87bed2721496924297
Source dataset
uspto-grants-2008_08
Patent number
US07411071B2

Reaction notes

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