Hydrochloric Acid → HCID 22258035, compound

HRID 1251574Notes

Reaction equation

HRID 1251574 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].C([NH:8][C:9](=[O:36])[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11]1[S:12][C:13]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[CH:14]C=1C(OCC)=O)(=O)C.Cl>C(O)C>[CH3:34][CH:33]([CH3:35])[CH2:32][N:10]1[C:11]2[S:12][C:13]([CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)=[CH:14][C:3]=2[C:2](=[O:1])[NH:8][C:9]1=[O:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxide2×HCID 5282537HCID 5282537, compound

Product 1

HCID 22258035HCID 22258035, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (0.036 g) was added to a solution of N′-acetyl-N-(2-methylpropyl)-N-[3-ethoxycarbonyl-5-(1-naphthalenylmethyl)-2-thienyl]urea (0.20 g) in ethanol (4 ml). The mixture was stirred for 3 hours then further sodium ethoxide (0.036 g) was added. After a further 3 hours, the mixture was poured into hydrochloric acid (2M, 20 ml) and extracted with ethyl acetate (2×20 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residua l solid was recrystallised from ethyl acetate/hexane to give the title compound (0.105 g).

Workup

  1. waitAfter a further 3 hours
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residua l solid was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4ba331cfcb284bfd9a161053a21f6536
Source dataset
uspto-grants-2002_01
Patent number
US06342502B1

Reaction notes

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