Thionyl Chloride → HCID 25073245, compound

HRID 1035678Notes

Reaction equation

HRID 1035678 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)[CH:8]=2)[C:3]=1[C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](O)=[O:23].S(Cl)(Cl)=O.[CH3:32][C:33]1[S:37][C:36]([NH2:38])=[N:35][N:34]=1>COCCOC.ClCCl>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)[CH:8]=2)[C:3]=1[C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([NH:38][C:36]1[S:37][C:33]([CH3:32])=[N:34][N:35]=1)=[O:23]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-HCID 25069442HCID 25069442, compound

Product 1

HCID 25073245HCID 25073245, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To 3-(2-hydroxy-6-(3-hydroxyphenyl)naphthalene-1-yl)benzoic acid (220 mg, 0.62 mmol, 1 eq), which is dissolved under a nitrogen atmosphere in 5 ml of dry DME, thionyl chloride (600 μl) is added, and the mixture is stirred at RT for 2 h. After the excess thionyl chloride has been removed in vacuum on a rotary evaporator, the residue is dissolved in dry THF and added dropwise to a suspension of 5-methyl-1,3,4-thiadiazole-2-amine (42.6 mg, 0.74 mmol, 1.2 eq) in dry dichloromethane cooled at 0° C. The reaction mixture is stirred at RT over night, followed by removing the solvent on a rotary evaporator. Purification of the raw product by column chromatography with dichloromethane/methanol 95/5 as the eluent yielded the desired compound in a yield of 47%, 132 mg.

Workup

  1. customAfter the excess thionyl chloride has been removed in vacuum on a rotary evaporator
  2. dissolutionthe residue is dissolved in dry THF
  3. temperaturecooled at 0° C
  4. stirringThe reaction mixture is stirred at RT over night
  5. customby removing the solvent
  6. customon a rotary evaporator
  7. customPurification of the raw product by column chromatography with dichloromethane/methanol 95/5 as the eluent

Sources & evidence

ORD record
ord-46198c8b0d2a4552bd077d9c5cb02d4a
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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