Bromine → 7-Cyclohexyl-4-methoxy-benzothiazol-2-ylamine

HRID 1582141Notes

Reaction equation

HRID 1582141 reaction equation
[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([O:17][CH3:18])=[C:11]([NH:13][C:14]([NH2:16])=[S:15])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.BrBr>C(Cl)(Cl)Cl.ClCCl>[CH:1]1([C:7]2[C:12]3[S:15][C:14]([NH2:16])=[N:13][C:11]=3[C:10]([O:17][CH3:18])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 24408BromineHCID 22719554HCID 22719554, compound

Product 1

HCID 227195747-Cyclohexyl-4-methoxy-benzothiazol-2-ylamineYield 68.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.9 g (0.0034 Mol) (5-cyclohexyl-2-methoxy-phenyl)-thiourea in 18 ml chloroform were added 0.2 ml (0.0041 Mol) bromine, dissolved in 4.5 ml chloroform and heated to reflux for 16 h. The reaction mixture was diluted with dichloromethane, extracted with sat. aqueous potassium carbonate and brine, dried over sodium sulfate and evaporated to dryness in vacuo. The residue was crystallized from ethyl acetate/diethyl ether to yield 0.61 g (68%) of 7-cyclohexyl-4-methoxy-benzothiazol-2-ylamine as an off-white solid; F.p.: 199-200° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. extractionextracted with sat. aqueous potassium carbonate and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness in vacuo
  6. customThe residue was crystallized from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-86025634d689411298f277f91da91fa2
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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