Sodium Sulfide → HCID 44132888, compound

HRID 1916272Notes

Reaction equation

HRID 1916272 reaction equation
Cl[C:2]1[C:3]([C:20]#[N:21])=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[C:10](=[O:11])[NH:9][C:8](=[O:12])[NH:7][C:6]=2[N:13]=1.[S-2:22].[Na+].[Na+].Cl[CH2:26][C:27]1[N:28]=[C:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[S:30][CH:31]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.O>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([C:29]2[S:30][CH:31]=[C:27]([CH2:26][S:22][C:2]3[C:3]([C:20]#[N:21])=[C:4]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:5]4[C:10](=[O:11])[NH:9][C:8](=[O:12])[NH:7][C:6]=4[N:13]=3)[N:28]=2)=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 14804Sodium SulfideHCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 58158146HCID 58158146, compound

Product 1

HCID 44132888HCID 44132888, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

100 mg (0.275 mmol) of the compound from Example 9A were dissolved in 0.55 ml of DMF, 25 mg (0.329 mmol) of sodium sulfide were added and the mixture was stirred at RT overnight. The reaction solution was then diluted with 1 ml of DMF, 74 mg (0.302 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 69 mg (0.825 mmol) of sodium bicarbonate were added and the mixture was stirred at RT for 45 min. Water was added to the reaction mixture. The precipitate formed was triturated with THF/Methanol (5 ml/2 ml) and then filtered off. This gave 21 mg (15% of theory) of the product as a solid. For further purification, the filtrate was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% TFA). This gave another 70 mg (50% of theory) of the product.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at RT for 45 min
  3. customThe precipitate formed
  4. customwas triturated with THF/Methanol (5 ml/2 ml)
  5. filtrationfiltered off
  6. customFor further purification
  7. customthe filtrate was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% TFA)
  8. customThis gave another 70 mg (50% of theory) of the product

Sources & evidence

ORD record
ord-9ca25adfa1bf418a8a05737dd5384ecb
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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