Ethyl 1-bromocyclobutanecarboxylate → HCID 178517981, compound

HRID 852778Notes

Reaction equation

HRID 852778 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-0b7708e015c947018d4e37eb80c582d2
Source dataset
uspto-grants-2007_08
Patent number
US07253196B2

Reaction notes

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