Bromine → HCID 178456992, compound

HRID 1975935Notes

Reaction equation

HRID 1975935 reaction equation
[Br:1]Br.Cl[C:4]1[S:12][C:11]2[S:10](=[O:14])(=[O:13])[N:9]=[C:8]([NH:15][CH:16]([CH3:18])[CH3:17])[NH:7][C:6]=2[CH:5]=1>C(O)(=O)C>[Br:1][C:4]1[S:12][C:11]2[S:10](=[O:14])(=[O:13])[N:9]=[C:8]([NH:15][CH:16]([CH3:18])[CH3:17])[NH:7][C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 1784569956-chloro-1,1-dioxo-N-propan-2-yl-4H-thieno[3,2-e][1,2,4]thiadiazin-3-amine

Product 1

HCID 178456992HCID 178456992, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Bromine (1.26 ml, 25 mmol) was added dropwise to a solution of 6-chloro-3-isopropylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (2.3 g, 8.2 mmol) in 25 ml of acetic acid and the mixture was stirred for 48 h at 100° C. in a sealed flask. The cooled mixture was evaporated to dryness and the residue which consisted of two major products was triturated with water to give a solid, which was recrystallised from ethyl acetate/methanol with decolorising charcoal to afford 538 mg (20%) of the title compound. An analytically pure sample was obtained by preparative hplc on a Source RPC 15 column using acetonitrile/water (20:80) with 0.1% TFA as eluent; mp 282-283° C.; 1H-NMR (DMSO-d6): δ1.16 (d, 6H), 3.86 (m, 1H), 7.14 (s, 1H), 7.18 (br, 1H), 10.74 (s, 1H); MS: m/e 323/325 (M+); (C8H10N3Br1O2S2); calc C, 29.64; H, 3.11; N, 12.96; found C, 29.49; H, 3.04; N, 12.59.

Workup

  1. customThe cooled mixture was evaporated to dryness
  2. customwas triturated with water
  3. customto give a solid, which
  4. customwas recrystallised from ethyl acetate/methanol with decolorising charcoal

Sources & evidence

ORD record
ord-6bac45ccb63e468482061e191489156c
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

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