Chloroform → 5-Bromo-7-methyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalene-2-carboxylic acid ethyl ester

HRID 30261Notes

Reaction equation

HRID 30261 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:13][CH:12]2[CH:8]([CH:9]([CH3:17])[C:10]3[CH:16]=[CH:15][S:14][C:11]=32)[CH2:7]1)=[O:5])[CH3:2].C(Cl)(Cl)Cl.C1C(=O)N([Br:29])C(=O)C1>CC(O)=O>[CH2:1]([O:3][C:4]([N:6]1[CH2:13][CH:12]2[CH:8]([CH:9]([CH3:17])[C:10]3[CH:16]=[C:15]([Br:29])[S:14][C:11]=32)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 67184N-bromobutanimideHCID 1317270357-Methyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalene-2-carboxylic acid ethyl ester

Product 1

HCID 1317270345-Bromo-7-methyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalene-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product from step i) (204 mg, 0.81 mmol) in AcOH (2 ml) and CHCl3 (2 ml) was treated with NBS (152 mg, 0.85 mmol) at 22° C. for 30 minutes. Next, the reaction was carefully quenched with sat. NaHCO3 (10 ml), extracted with EtOAc (2×75 ml) and the combined organic layers were dried (MgSO4). The crude product was filtered through a plug of silica gel using hexanes:EtOAc (50:50) to give the subtitle compound. MS calculated for C13H16BrNO2S+H 330, observed 332.

Workup

  1. customNext, the reaction was carefully quenched with sat. NaHCO3 (10 ml)
  2. extractionextracted with EtOAc (2×75 ml)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationThe crude product was filtered through a plug of silica gel

Sources & evidence

ORD record
ord-0f67d326358948cc9965a2babeb0fbad
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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