HCID 22726891, compound → HCID 22726781, compound

HRID 2085974Notes

Reaction equation

HRID 2085974 reaction equation
C([NH:9][C:10]([NH:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[S:11])(=O)C1C=CC=CC=1>[OH-].[Na+]>[C:19]([O:18][C:16]([NH:15][CH2:14][CH2:13][NH:12][C:10]([NH2:9])=[S:11])=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

3

Reactant 1

HCID 22726891HCID 22726891, compound

Product 1

HCID 22726781HCID 22726781, compoundYield 1,046.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

N-benzoyl-N′-(2-t-butyloxycarbonylaminoethyl)thiourea (1.50 g, 0.44 mmol) was suspended in aqueous sodium hydroxide solution (22 mL, 2.0 M) and heated to 50° C. with stirring for 1 hour, which resulted in dissolution of starting material and consequent formation of precipitate. Reaction mixture was extracted with ethyl. acetate and the organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford solid residue of title product (1.01 g), which was used for next step without further purification. 1H NMR (CDCl3/CD3OD) δ 1.40 (s, 9H), 3.20 (m, 4H), 3.55 (m, 2H).

Workup

  1. customwhich resulted in dissolution of starting material and consequent formation of precipitate
  2. customReaction mixture
  3. extractionwas extracted with ethyl
  4. dry with materialacetate and the organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dbb0f29db0b340bcb1b919fb2f4875ad
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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