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

HRID 354047Notes

Reaction equation

HRID 354047 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 mm 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 C8H7N2O4PSCIBr: 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-d99371362075452183cbbd40f1c10054
Source dataset
uspto-grants-2004_06
Patent number
US06756360B1

Reaction notes

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