2-Aminothiazole → benzyl N-(1,3-thiazol-2-yl)carbamate

HRID 2279432Notes

Reaction equation

HRID 2279432 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C(N(CC)CC)C.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>>[CH2:18]([O:17][C:15](=[O:16])[NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 5113639benzyl N-(1,3-thiazol-2-yl)carbamateYield 70%

Procedure

To a stirred solution of 2-aminothiazole (AA1-A, 3.0 g, 30.0 mmol) and triethylamine (6.30 mL, 45.0 mmol) at 0° C. was added benzyl chloroformate (5 mL, 36 mmol). The reaction was stirred at RT O/N. The reaction mixture was washed with a saturated aqueous solution of NaHCO3, then water and concentrated to dryness under reduced pressure. The resulting yellow solid was crystallized from ethanol to afford AA1-2 in 70% yield.

Workup

  1. washThe reaction mixture was washed with a saturated aqueous solution of NaHCO3
  2. concentrationwater and concentrated to dryness under reduced pressure
  3. customThe resulting yellow solid was crystallized from ethanol
  4. customto afford AA1-2 in 70% yield

Sources & evidence

ORD record
ord-1b383bf2754e46beb060a6433f482530
Source dataset
uspto-grants-2015_09
Patent number
US09133235B2

Reaction notes

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