Thiourea → 871716-68-6

HRID 1685077Notes

Reaction equation

HRID 1685077 reaction equation
Cl[CH2:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=O.[NH2:17][C:18]([NH2:20])=[S:19]>C(O)C>[NH2:20][C:18]1[S:19][CH:2]=[C:3]([CH:5]2[CH2:9][CH2:8][CH2:7][N:6]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[N:17]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 4072501Tert-butyl 2-(2-chloroacetyl)pyrrolidine-1-carboxylate

Product 1

HCID 44118268871716-68-6

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol (20 mL) solution of tert-butyl 2-(2-chloroacetyl)pyrrolidine-1-carboxylate (1.08 g, 4.4 mol) and thiourea (334 mg, 4.4 mmol) was stirred at 55 C for 70 hours. Upon completion of the condensation, the solution was evaporated. The solid was dissolved in CH2Cl2 (100 mL). It was washed with dilute NaHCO3 solution, dried and evaporated. Recrystallization from CH2Cl2/hexane afforded tert-butyl 2-(2-aminothiazol-4-yl)pyrrolidine-1-carboxylate. 1H NMR (400 MHz, CDCl3): mixture of rotamers: δ 8.81 (s, 2H, br), 6.22 and 6.15 (2s, 1H), 4.84 and 4.78 (2s, 1H), 3.62 and 3.44 (2m, 2H), 2.4-1.8 (m, 4H), 1.46 and 1.36 (2s, 9H). MS (ES+): M/Z 270 (M+H)+, 170 (M−C5H8O2)+.

Workup

  1. customUpon completion of the condensation
  2. customthe solution was evaporated
  3. dissolutionThe solid was dissolved in CH2Cl2 (100 mL)
  4. washIt was washed with dilute NaHCO3 solution
  5. customdried
  6. customevaporated
  7. customRecrystallization from CH2Cl2/hexane

Sources & evidence

ORD record
ord-0ea6ae08f8b14dd9bc7670566ca6aff0
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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