Dimethylformamide → HCID 136380449, compound

HRID 1294725Notes

Reaction equation

HRID 1294725 reaction equation
[C:1]1([NH:11][C:12](=[S:15])[NH:13][NH2:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:16]([C:19]1[C:20](O)=[C:21]([CH:24]=[CH:25][CH:26]=1)C=O)([OH:18])=[O:17].S(NN)(C1C=CC(C)=CC=1)(=O)=O.CN(C)[CH:42]=[O:43]>>[C:16]([C:19]1[CH:26]=[CH:25][C:24]([CH:21]=[N:14][NH:13][C:12]([NH:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[S:15])=[C:42]([OH:43])[CH:20]=1)([OH:18])=[O:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 15303P-ToluenesulfonylhydrazideHCID 69117Isophthalaldehydic acid, 2-hydroxy-HCID 2760175N-(Naphthalen-1-yl)hydrazinecarbothioamide

Product 1

HCID 136380449HCID 136380449, compoundYield 81%

Procedure

A solution of 4-(naphth-1-yl)-3-thiosemicarbazide (38 mg, 0.175 mmol) and 4 carboxy-2-hydroxybenzaldehyde (35 mg, 0.211 mmol) in dimethylformamide (2 mL) was shaken with 4 Å molecular sieves for 2.5 h. PS-TsNHNH2 resin (50 mg, 0.147 mmol) was added, shaking continued for 1 h, then the resin filtered off. Water was added to the filtrate and the precipitated solid was filtered, washed (water, ether) and dried to give the title compound (52 mg, 81%) as a solid. MS (ES+) m/e 366 [M+H]+.

Workup

  1. filtrationthe resin filtered off
  2. additionWater was added to the filtrate
  3. filtrationthe precipitated solid was filtered
  4. washwashed (water, ether)
  5. customdried

Sources & evidence

ORD record
ord-7c87687153834fc5bbd93e0fd6d56fcc
Source dataset
uspto-grants-2007_07
Patent number
US07241783B2

Reaction notes

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