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

HRID 970715Notes

Reaction equation

HRID 970715 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 C8H8N2O4PSBr: 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-d09d088212e34923be958892cf12b21a
Source dataset
uspto-grants-2007_12
Patent number
US07312219B2

Reaction notes

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