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

HRID 970716Notes

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

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

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

Sources & evidence

ORD record: ord-0323c84f00d640cf86c9378fc79472a5
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312219B2

Reaction notes

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