Bromine → 2-Amino-7-bromo-6,7-dihydro-4H-cyclohepta[d]thiazol-8(5H)-one

HRID 1942997Notes

Reaction equation

HRID 1942997 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.[Br:13]Br>C(O)(=O)C>[NH2:1][C:2]1[S:3][C:4]2[C:11](=[O:12])[CH:10]([Br:13])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 251308282-amino-4H,5H,6H,7H,8H-cyclohepta[d][1,3]thiazol-8-one

Product 1

HCID 251304942-Amino-7-bromo-6,7-dihydro-4H-cyclohepta[d]thiazol-8(5H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 26z (1.96 g, 7.45 mmol; HBr salt form) in glacial acetic acid (70 mL) was treated dropwise with Br2 (421 uL, 8.2 mmol). The reaction mixture was stirred at room temperature for 30 min. The crude product was collected by filtration, washed with cold acetone, and dried to yield 27z which was used in the next step without purification (1.98 g, 78%). 1H NMR (600 MHz, 2 DMSO-d6): δ 8.71 (br s, 2H), 5.11 (dd, J=6.9 Hz, 3.3 Hz, 1H), 3.08-2.90 (m, 2H), 2.473 2.39 (m, 1H), 2.28-2.20 (m, 1H), 2.14 (dd, J=10.1 Hz, 2.3 Hz, 1H), 1.98-1.90 (m, 1H). MS (ESI) m/z [M+H]+ 260.92; [(M+2)+H]+ 262.88. 5 6

Workup

  1. filtrationThe crude product was collected by filtration
  2. washwashed with cold acetone
  3. customdried

Sources & evidence

ORD record
ord-a47fab81615544edb52ed9dd64143ab0
Source dataset
uspto-grants-2013_03
Patent number
US08389736B2

Reaction notes

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