Phosgene → HCID 117664692, compound

HRID 2199497Notes

Reaction equation

HRID 2199497 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:10]([O:17][CH3:18])[CH:9]=[C:8](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.Cl[C:35](Cl)=[O:36].[NH2:38][NH2:39]>ClCCl>[NH:38]([C:35]([O:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:10]([O:17][CH3:18])[CH:9]=[C:8](/[CH:19]=[CH:20]/[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:36])[NH2:39]

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 9321HydrazineHCID 117664395HCID 117664395, compound

Product 1

HCID 117664692HCID 117664692, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve compound 8 (1.0 g, 2.84 mmol) and triethylamine (0.43 g, 4.26 mmol) in dichloromethane (30 ml), add dropwise chloroformyl chloride at 0° C. (0.40 g, 3.98 mmol), after finishing the addition, react at room temperature for 4h, cool the solution to 0° C., add dropwise hydrazine (0.2 g, 5.68 mmol) dichloromethane solution slowly at room temperature, after finishing the addition react at room temperature until finishing the reaction, subsequently wash the solution successively with water, dilute hydrochloric acid and saturated brine, dry the organic layer over anhydrous magnesium sulfate. Filter and concentrate the solution, and redissolve the residue, feed the solution into a chromatographic column, evaporate the solvent in the eluent to obtain a white solid as the target product (0.87 g, 75%). 1H NMR (400 MHz, DMSO-d6): 1.78 (s, 3H), 1.81 (s, 3H), 3.24 (d, J=7.6 Hz, 2H), 3.78 (s, 3H), 3.87 (s, 3H), 45 (s, 2H), 6.73 (s, 1H), 6.79 (d, J=16.0 Hz, 1H), 7.24 (d, J=16.0 Hz, 1H), 7.34 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.42 (s, 1H), 7.45 (t, J=7.6 Hz, 2H).

Workup

  1. additionthe addition
  2. additionthe addition
  3. customreact at room temperature
  4. customthe reaction
  5. washsubsequently wash the solution successively with water, dilute hydrochloric acid and saturated brine
  6. dry with materialdry the organic layer over anhydrous magnesium sulfate
  7. filtrationFilter
  8. concentrationconcentrate the solution
  9. dissolutionredissolve the residue
  10. customevaporate the solvent in the eluent

Sources & evidence

ORD record
ord-6abf884cc1de4575a9b335d63298717c
Source dataset
uspto-grants-2016_06
Patent number
US09359298B2

Reaction notes

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