N-bromobutanimide → HCID 18963856, compound

HRID 2226978Notes

Reaction equation

HRID 2226978 reaction equation
[Cl:1][C:2]1[C:6]2[N:7]=[C:8]([CH3:10])[S:9][C:5]=2[S:4][CH:3]=1.C1C(=O)N([Br:18])C(=O)C1>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH2:10][C:8]1[S:9][C:5]2[S:4][CH:3]=[C:2]([Cl:1])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18963857HCID 18963857, compound

Product 1

HCID 18963856HCID 18963856, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 7187Benzoyl PeroxideCatalyst

Conditions

Temperature
75 °C

Procedure

To a solution of 310 mg(1.62 mmol) of 6-chloro-2-methylthieno[3,2-d]thiazole (from Step 2) and 10 mg of benzoyl peroxide in 15 ml of CC14 was added 306 mg(1.72 mmol) of NBS at r.t. The mixture was stirred at 75° C. under radiation from a sunlamp for 30 min. The solid was filtered, the solution was evaporated to dryness and the residue purified on silica gel with hexane/EtOAc=8:1 to give 300 mg (69%) of the title product. 1H NMR (CDCl3) 7.35(s, 1H), 4.80(s,2H).

Workup

  1. filtrationThe solid was filtered
  2. customthe solution was evaporated to dryness
  3. customthe residue purified on silica gel with hexane/EtOAc=8:1

Sources & evidence

ORD record
ord-4c0ca97bf2e14d4bac940954c24be3c8
Source dataset
uspto-grants-1994_09
Patent number
US05350760

Reaction notes

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