Bromine → 4-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-ylmethyl)-benzothiazole-2,7-diamine

HRID 51892

Reaction equation

HRID 51892 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:17])[CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:5][C:4]=1[NH:18][C:19]([NH2:21])=[S:20].BrBr>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]2[N:18]=[C:19]([NH2:21])[S:20][C:5]=2[C:6]([N:9]([CH3:17])[CH2:10][CH:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 22736994HCID 22736994, compound

Product 1

HCID 227370054-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-ylmethyl)-benzothiazole-2,7-diamineYield 98.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.5 g (0.53 mmol) {2-methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea were dissolved in 15 ml chloroform and at room temperature 0.025 ml (0.5 mmol) Br2 were added slowly. After 24 hrs of reflux the mixture was concentrated in vactio and the residue suspended in water. Sodium bicarbonate solution was added until the pH was 10, and the crystals were collected by filtration. These were subjected to column chromatography (1/1 hexane/ethyl acetate) to afford 0.16 g (10%) of 4-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-ylmethyl)-benzothiazole-2,7-diamine as brown solid. ES-MS m/e (%): 308 (M+H+, 100).

Workup

  1. additionwere added slowly
  2. temperatureAfter 24 hrs of reflux the mixture
  3. concentrationwas concentrated in vactio
  4. additionSodium bicarbonate solution was added until the pH was 10
  5. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-ff07b51b7c5147e79cbabb50bbbdd643
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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