Bromine → HCID 22735343, compound

HRID 1279219Notes

Reaction equation

HRID 1279219 reaction equation
BrBr.[F:3][C:4]([F:18])([F:17])[O:5][C:6]1[CH:15]=[C:14]2[C:9]([NH:10][CH2:11][C:12](=[O:16])[NH:13]2)=[CH:8][CH:7]=1.[S-:19][C:20]#[N:21].[K+]>C(O)(=O)C>[NH:21]=[C:20]1[N:10]2[CH2:11][C:12](=[O:16])[NH:13][C:14]3[CH:15]=[C:6]([O:5][C:4]([F:3])([F:17])[F:18])[CH:7]=[C:8]([C:9]=32)[S:19]1

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 22735226HCID 22735226, compound

Product 1

HCID 22735343HCID 22735343, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

The procedure is carried out as in Example 23, but starting with 1.1 g of bromine in 3.5 ml of acetic acid, 1.6 g of 7-trifluoromethoxy-3,4-dihydro-1H-quinoxalin-2-one and 1.54 g of potassium thiocyanate in 20 ml of acetic acid. The product obtained (1.8 g) is purified by chromatography on a silica gel column, eluting with a mixture of dichloromethane and methanol (99-1 by volume). 0.3 g of 2-imino-8-trifluoromethoxy-2H,4H-thiazolo[3,4,5-de]quinoxalin-5(6H)-one is thus obtained in the form of a yellow solid melting at 255° C. [Analysis C10H6F3N3O2S, % calculated C, 41.53; H, 2.09; F, 19.71; N, 14.53, O, 11.06; S, 11.09; % found C, 41.00; H, 1.7; F, 19.2; N, 14.50; S, 11.6].

Workup

  1. customThe product obtained (1.8 g)
  2. customis purified by chromatography on a silica gel column
  3. washeluting with a mixture of dichloromethane and methanol (99-1 by volume)

Sources & evidence

ORD record
ord-1482b5a7f9684ab2b32556750f7ee13a
Source dataset
uspto-grants-2002_09
Patent number
US06448241B1

Reaction notes

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