2-Amino-4,5,6,7-tetrahydrobenzothiazole → HCID 3715134, compound

HRID 928317Notes

Reaction equation

HRID 928317 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[S:11]1[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=2[N:13]=[C:12]1[NH2:20]>N1C=CC=CC=1.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:20][C:12]2[S:11][C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[N:13]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 180462-Amino-4,5,6,7-tetrahydrobenzothiazoleHCID 685154-Bromobenzoyl chloride

Product 1

HCID 3715134HCID 3715134, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

4-Bromobenzoyl chloride (1.5 g, 6.83 mmol) and 4,5,6,7-Tetrahydro-1,3-benzothiazol-2-amine (1.054 g, 6.83 mmol) were dissolved in Pyridine (15 ml) and stirred at 50° C. for 1.5 h. The reaction mixture was cooled to room temperature and poured in water. The solid formed was filtered, washed with water. The solids were co-evaporated with toluene twice to afford 1.8 g of 4-bromo-N-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)benzamide (78%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solid formed
  3. filtrationwas filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-fc8798bc8b2c4f0096283c6d198f0ea2
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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