Triethylamine → Carbamic acid, (5-formyl-2-thiazolyl)-, phenylmethyl ester

HRID 1822883Notes

Reaction equation

HRID 1822883 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=1.C(N(CC)CC)C.[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[CH2:16]([O:23][C:24]([NH:1][C:2]1[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 27377982-Amino-1,3-thiazole-5-carbaldehyde

Product 1

HCID 22170759Carbamic acid, (5-formyl-2-thiazolyl)-, phenylmethyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g (7.8 mmol) of 2-amino-5-formyl-1,3-thiazole was dissolved in 25 ml of tetrahydrofuran and 1.35 ml (9.36mmol) of triethylamine and 1.33 ml (9.36 mmol) of benzylchloroformate were added at 0° C. under stirring. After 8 hours at room temperature the solvent was evaporated, the residue redissolved with methylene chloride and washed with saturated tartaric acid and then with water. The solvent was dried over anhydrous sodium sulfate and evaporated. The residue was purified by chromatography on silica gel using cyclohexane-ethylacetate as eluent to give 1.3 g (65% yield) of the title compound.

Workup

  1. customAfter 8 hours at room temperature the solvent was evaporated
  2. dissolutionthe residue redissolved with methylene chloride
  3. washwashed with saturated tartaric acid
  4. dry with materialThe solvent was dried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c0ccc45845534722bed60d2ffa6ed06a
Source dataset
uspto-grants-2006_05
Patent number
US07037929B1

Reaction notes

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