Triethylamine → HCID 178503953, compound

HRID 1477671Notes

Reaction equation

HRID 1477671 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([NH:12][C:13]([S:15][CH3:16])=[NH:14])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24]([O:27][CH2:28][C:29](Cl)=[O:30])(=[O:26])[CH3:25]>ClCCl>[C:24]([O:27][CH2:28][C:29]([N:14]=[C:13]([NH:12][C:10]([NH:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)=[O:11])[S:15][CH3:16])=[O:30])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 140668422HCID 140668422, compound

Product 1

HCID 178503953HCID 178503953, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (2.0 mL) of methyl N-({[(4-chlorobenzen-1-yl)methyl]amino}carbonyl)-carbamimidothioate (257 mg, 1.00 mmol) synthesized in Reference Synthesis Example 326, triethylamine (279 μL, 2.00 mmol) and 2-chloro-2-oxoethyl acetate (162 μL, 1.50 mmol) were added and the resultant mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (221 mg, yield 62%).

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. customthe reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-039f8f60cd9b4ec0a6b74fd0504b2138
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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