Bromine → 7-Chloro-4-methoxy-1,3-benzothiazol-2-amine

HRID 2297028Notes

Reaction equation

HRID 2297028 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[NH:10][C:11]([NH2:13])=[S:12].BrBr>C(Cl)(Cl)Cl>[NH2:13][C:11]1[S:12][C:5]2[C:6]([Cl:9])=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=2[N:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 2732660N-(5-Chloro-2-methoxyphenyl)thiourea

Product 1

HCID 136667137-Chloro-4-methoxy-1,3-benzothiazol-2-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of 1-(2-methoxy-5-chlorophenyl)-2-thiourea (1 mmole) in chloroform (10 mL) was cooled to 10° C. and treated with bromine (2.2 mmole) in chloroform (10 mL). The reaction was stirred at 10° C. for 20 min and at room temperature for 0.5 h. The resulting suspension was heated at reflux for 0.5 h. The precipitate was collected via filtration (washed with CH2Cl2) to give 2-amino-4-methoxy-7-chlorobenzothiazole which was subjected to Steps A, B, C and D of Example 34 to give 2-amino-4-phosphonomethoxy-6-bromo-7-chloro benzothiazole (35.1). mp>220° C.(dec.). Anal. Calcd. for C8H7N2O4PSClBr: C:25.72; H:1.89; N:7.50. Found: C:25.66; H:1.67; N:7.23.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 0.5 h
  3. filtrationThe precipitate was collected via filtration (washed with CH2Cl2)

Sources & evidence

ORD record
ord-ec44c92bd8164fd0b1bbf2cb0a232271
Source dataset
uspto-grants-2002_12
Patent number
US06489476B1

Reaction notes

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