N-bromobutanimide → HCID 67241539, compound

HRID 1028142Notes

Reaction equation

HRID 1028142 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Cl:9][C:10]1[N:11]=[C:12]([N:15]2[CH2:21][CH2:20][CH2:19][NH:18][C:17](=[O:22])[CH2:16]2)[S:13][CH:14]=1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[Br:8][C:14]1[S:13][C:12]([N:15]2[CH2:21][CH2:20][CH2:19][NH:18][C:17](=[O:22])[CH2:16]2)=[N:11][C:10]=1[Cl:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67241715HCID 67241715, compound

Product 1

HCID 67241539HCID 67241539, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

n-bromosuccinimide (80 mg, 0.449 mmol) was combined with a solution of 4-(4-chloro-1,3-thiazol-2-yl)-1,4-diazepan-2-one (100 mg, 0.432 mmol) in CHCl3 (6 ml) and stirred at 23° C. for 8 minutes. The solution became dark was immediately diluted with ethyl acetate, and washed successively with aq. sodium thiosulfate (sat.), aq. NaHCO3 (sat.) and brine. The organic fraction was dried (Na2SO4), filtered and concentrated to afford 4-(5-bromo-4-chloro-1,3-thiazol-2-yl)-1,4-diazepan-2-one (75 mg, 0.241 mmol, 55.9% yield) as a yellow oil of sufficient purity for subsequent transformations.

Workup

  1. washwashed successively with aq. sodium thiosulfate (sat.), aq. NaHCO3 (sat.) and brine
  2. dry with materialThe organic fraction was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5c1651c3149849aead9544284f905d2f
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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