Water → HCID 2828894, compound

HRID 1819744Notes

Reaction equation

HRID 1819744 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)=[O:14].O>C(O)C>[BrH:11].[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 692722-Bromo-4'-methylacetophenoneHCID 178418395HCID 178418395, compound

Product 1

HCID 2828894HCID 2828894, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-mercaptobenzothiazole (570 mg, 3.34 mmol) and 2-bromo-4′-methylacetophenone (870 mg, 3.67 mmol) was refluxed in ethanol (15 mL) for 90 minutes. The solution was cooled in the fridge to give a yellow solid in 18% yield: mp 76-78° C.; 1H-NMR (DMSO-d6) 2.42 (s, 3H), 5.15 (s, 2H), 7.36 (t, 1H), 7.41 (d, 2H), 7.44 (t, 1H), 7.78 (d, 1H), 8.00 (m, 3H); Anal. (C16H14BrNOS2½ H2O) C, H, N.

Workup

  1. temperatureThe solution was cooled in the fridge
  2. customto give a yellow solid in 18% yield

Sources & evidence

ORD record
ord-e440b55a09d34a07bc622b169cd38464
Source dataset
uspto-grants-2009_10
Patent number
US07601846B2

Reaction notes

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