Ethyl 1-bromocyclobutanecarboxylate → HCID 178517981, compound

HRID 1158088Notes

Reaction equation

HRID 1158088 reaction equation
[CH:1]1([NH:8][C:9]([NH2:11])=[S:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:13]1([C:17](OCC)=[O:18])[CH2:16][CH2:15][CH2:14]1>C(N(CC)C(C)C)(C)C.C(O)C>[CH:1]1([NH:8][C:9]2[S:10][C:13]3([C:17](=[O:18])[N:11]=2)[CH2:16][CH2:15][CH2:14]3)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 97595Ethyl 1-bromocyclobutanecarboxylateHCID 13433274N-Cycloheptylthiourea

Product 1

HCID 178517981HCID 178517981, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 1-cycloheptylthiourea (0.255 g, 1.48 mmol) and ethyl 1-bromocyclobutanecarboxylate (0.25 mL, 1.48 mmol, Aldrich) in N,N-diisopropylethylamine (0.5 mL) and ethanol (1.0 mL) was heated in a sealed tube in a microwave oven (Emrys Optimizer from Personal Chemistry) at 155° C. for 2 h, then at 170° C. for 1.5 h. After removing the low-boiling solvents in vacuo, the residue was partitioned between EtOAc and water. The organic portion was separated, washed with brine, and conc. in vacuo. The residue was purified by flash column chromatography (0 to 35% of EtOAc in hexanes) to give the title compound as a tan solid. MS m/z: 253.2 (M+H)+

Workup

  1. customAfter removing the low-boiling solvents in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. customThe organic portion was separated
  4. washwashed with brine
  5. customThe residue was purified by flash column chromatography (0 to 35% of EtOAc in hexanes)

Sources & evidence

ORD record
ord-a612b66d690f40abb89a5772e72fc736
Source dataset
uspto-grants-2010_10
Patent number
US07807700B2

Reaction notes

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