Hydrochloric Acid → 2,2,2-Trichloroethyl 2-(3-iodo-4-nitrobenzamido)acetate

HRID 1399433Notes

Reaction equation

HRID 1399433 reaction equation
[ClH:1].C(N(CC)CC)C.[I:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13](Cl)=[O:14].[N+](C1C=C([N+]([O-])=O)C=CC=1C([NH:29][CH2:30][C:31]([O:33][CH2:34]C1C=CC=CC=1)=[O:32])=O)([O-])=O.[CH2:48]([Cl:50])[Cl:49]>O1CCOCC1>[I:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13]([NH:29][CH2:30][C:31]([O:33][CH2:34][C:48]([Cl:1])([Cl:50])[Cl:49])=[O:32])=[O:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 86713106Benzyl 2-(2,4-dinitrobenzamido)acetateHCID 867131113-Iodo-4-nitrobenzoyl chloride

Product 1

HCID 867131102,2,2-Trichloroethyl 2-(3-iodo-4-nitrobenzamido)acetateYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution 2,2,2-trichloroethyl N-Boc glycinate (1.25 g, 4.08 mmol) in DCM (10 mL) was added HCl in dioxane (2N, 10 mL) and stirred at rt for 2 h. Solvents were removed under reduced pressure, and was dissolved in DCM (10 mL) and added triethylamine (1.48 mL, 10.23 mmol) at 0° C. A solution of 3-iodo-4-nitrobenzoyl chloride (prepared from 3-iodo-4-nitrobenzoic acid, 1 g and SOCl2, 10 mL) in DCM (10 mL) was added to the above reaction mixture at 0° C. Then the reaction mixture was stirred at rt for 3 h and worked-up as described in intermediate 1 to obtain the product as a cream color solid (1.28 g, 78%), mp 98-100° C. 1H NMR (400 MHz, CDCl3): δ 8.46 (1H, s), 7.90 (2H, s), 6.67 (1H, br s), 4.86 (2H, s), 4.23 (2H, d, J=5.2 Hz); LC-MS (negative ion mode): m/z 479 (M−H)−.

Workup

  1. customSolvents were removed under reduced pressure
  2. dissolutionwas dissolved in DCM (10 mL)
  3. stirringThen the reaction mixture was stirred at rt for 3 h

Sources & evidence

ORD record
ord-546bc20bc3094281bf2a11829ba33a93
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

Loading…