Bromotrimethylsilane → 2-Amino-4-phosphonomethyloxy-6-bromobenzothiazole

HRID 354046Notes

Reaction equation

HRID 354046 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]([O:12][CH2:13][P:14]([O:19]CC)([O:16]CC)=[O:15])[C:5]=2[N:6]=1.C[Si](Br)(C)C>C(Cl)Cl>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]([O:12][CH2:13][P:14]([OH:19])([OH:16])=[O:15])[C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 545277422-Amino-4-diethylphosphonomethyloxy-6-bromobenzothiazole

Product 1

HCID 222806832-Amino-4-phosphonomethyloxy-6-bromobenzothiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-amino-4-diethylphosphonomethyloxy-6-bromobenzothiazole (1 mmole) in CH2Cl2(4 mL) was treated with TMSBr (10 mmole) at 0° C. After stirred for 8 h at room temperature the reaction was evaporated to dryness and the residue was taken into water (5 mL). The resulting precipitate was collected via filtration and washed with water to give 2-amino-4-phosphonomethyloxy-6-bromobenzothiazole (34.1) as white solid. mp >220° C. (dec.). Anal. Calcd. for C9H8N2O4PSBr: C:28.34; H:2.38; N:8.26. Found: C:28.32; H:2.24; N:8.06.

Workup

  1. customwas evaporated to dryness
  2. filtrationThe resulting precipitate was collected via filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-ba4b3823f2f74cf9b708f37b41cf74d5
Source dataset
uspto-grants-2004_06
Patent number
US06756360B1

Reaction notes

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