4-Hydroxybenzaldehyde → HCID 87309085, compound

HRID 384517Notes

Reaction equation

HRID 384517 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].[OH:26][S:27]([O-:29])=[O:28].[Na+]>CC#N>[S:27](=[O:26])([OH:29])[OH:28].[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 119872-ChlorobenzothiazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 87309085HCID 87309085, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chlorobenzothiazole (33.7 g, 199 mmol) in CH3CN (500 mL) was added 4-hydroxy benzaldehyde (24.3 g, 199 mmol) and K2CO3 (28 g, 199 mmol). The heterogeneous mixture was heated at reflux for 72 h and then cooled to rt. The solids were removed by filtration and washed with CH3CN (100 mL). To the filtrate was added an aqueous solution of NaHSO3 (26 g, 199 mmol, 66 mL water). After stirring for 3.5 h, the mixture was filtered and the wet cake was dried under vacuum overnight to afford the bisulfite complex (66 g, 92%) as a white powder. 1H NMR (500 MHz, DMSO-d6): 7.93 (d, J=8.0 Hz, 1H), 7.74 (d, J=8.0 Hz, 1H), 7.60-7.55 (m, 2H), 7.44-7.39 (m, 1H), 7.35-7.29 (m, 3H), 6.03 (d, J=5.2 Hz, 1H), 5.04 (d, J=5.2 Hz, 1H).

Workup

  1. temperatureThe heterogeneous mixture was heated
  2. temperatureat reflux for 72 h
  3. customThe solids were removed by filtration
  4. washwashed with CH3CN (100 mL)
  5. filtrationthe mixture was filtered
  6. customthe wet cake was dried under vacuum overnight
  7. customto afford the bisulfite complex (66 g, 92%) as a white powder

Sources & evidence

ORD record
ord-0881ba1dca8f4a4092bc174f0a69b995
Source dataset
uspto-grants-2013_02
Patent number
US08367719B2

Reaction notes

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