Triethylamine → HCID 136160556, compound

HRID 1930183Notes

Reaction equation

HRID 1930183 reaction equation
C(N(CC)CC)C.[OH:8]/[N:9]=[C:10](\[NH2:20])/[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[C:14]([CH3:19])[CH:13]=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>ClCCl>[OH:8]/[N:9]=[C:10](\[NH:20][C:22](=[O:23])[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)/[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[C:14]([CH3:19])[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 59627719HCID 59627719, compound2×

Product 1

HCID 136160556HCID 136160556, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.651 mL, 4.67 mmol) was added to (Z)—N′-hydroxy-2-(4-iodo-3-methylphenyl)acetimidamide (Intermediate 29-3; 1.13 g, 3.90 mmol) in dry dichloromethane (30 mL) at 0° C. The resulting yellow solution was stirred at 0° C. for 1 hour. Phenyl chloroformate (0.598 mL, 4.67 mmol) was added and the reaction mixture stirred at 0° C. for a further 1 hour. The solution was washed sequentially with saturated Na2CO3 (50 mL) and water (50 mL×2). The organic layer was dried over MgSO4, filtered and evaporated to afford (Z)-phenyl 1-(hydroxyimino)-2-(4-iodo-3-methylphenyl)ethylcarbamate (1.675 g, 105%) as crude product.

Workup

  1. stirringthe reaction mixture stirred at 0° C. for a further 1 hour
  2. washThe solution was washed sequentially with saturated Na2CO3 (50 mL) and water (50 mL×2)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5113dd4c8075424da00022bec705674e
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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