2-Bromopropanedial → HCID 86624700, compound

HRID 604915Notes

Reaction equation

HRID 604915 reaction equation
Br[CH:2]([CH:5]=O)[CH:3]=[O:4].C([O-])(=O)C.[Na+].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:26][C:27]([NH2:29])=[S:28])[CH:17]=[CH:18][C:19]=1[N:20]1[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]1>>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:26][C:27]2[S:28][C:2]([CH:3]=[O:4])=[CH:5][N:29]=2)[CH:17]=[CH:18][C:19]=1[N:20]1[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]1

Participants

4

Reactant 3

HCID 749452-BromopropanedialHCID 517045Sodium AcetateHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 86624700HCID 86624700, compoundYield 56%

Procedure

The title compound was prepared in analogy to example 1 step e) from 78 mg (0.5 mmol) bromomalonaldehyde, 82 mg (1 mmol) sodium acetate and 131 mg (0.5 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The solvent was evaporated. The reaction was diluted with water and extracted twice with ethyl acetate and twice with methylene chloride/methanol 9/1. The combined organic layers were washed with brine, dried over sodium sulphate, filtered and the solvent was evaporated under reduced pressure. The crude product was stirred diethyl ether to yield 88 mg (56%) of 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazole-5-carbaldehyde as a yellow solid. MS ISP (m/e): 315.1 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=11.35 (br s, 1H), 9.80 (s, 1H), 8.27 (s, 1H), 7.70 (s, 1H), 7.55 (s, 1H), 7.38 (d, 1H), 7.33 (d, 1H), 7.07 (s, 1H), 3.82 (s, 3H), 2.15 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. additionThe reaction was diluted with water
  3. extractionextracted twice with ethyl acetate and twice with methylene chloride/methanol 9/1
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-29806da286954612966a253500020503
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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