Dimethylcarbamoyl Chloride → HCID 13039016, compound

HRID 1759298Notes

Reaction equation

HRID 1759298 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][P:10]([O-:20])[O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.C([N:23]([CH2:26]C)[CH2:24]C)C.[CH3:28][N:29]([CH3:33])[C:30](Cl)=[O:31].[CH2:34]([O:36][C:37](=[O:39])C)[CH3:35]>C1C=CC=CC=1.C1CCCCC1>[CH2:34]([O:36][C:37](=[O:39])[CH2:28][N:29]([C:30]([N:23]([CH3:24])[CH3:26])=[O:31])[CH2:33][P:10]([O:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)([O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:20])[CH3:35]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 20358965HCID 20358965, compound

Product 1

HCID 13039016HCID 13039016, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8078CyclohexaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-methylene ethylglycinate trimer (2.88 g; 0.025 mol.) and di-(4-methoxyphenyl)phosphite (7.97 g; 0.025 mol.) in benzene was refluxed for one hour. Triethylamine (10.1 g; 0.1 mol.) was added to the reaction mixture and the resulting mixture was cooled to 0° C. in an ice bath. A solution of dimethylaminocarbonyl chloride (3.25 g; 0.303 mol.) in benzene was added dropwise to the reaction mixture. The reaction mixture was allowed to warm to 26° C. and then was refluxed for 25 hours. The reaction mixture was filtered and the filtrate concentrated in vacuo producing a crude product. The crude product was purified using a chromatographic system comprising of a silica gel column and a 3:2 mixture (by volume) of ethylacetate:cyclohexane as the eluant to yield ethyl-N-(N',N'-dimethyaminocarbonyl)-N-[bis(4-methoxyphenoxy)phosphinylmethyl]glycinate (3.25 g; 27% yield) represented by the formula ##STR13## as an oil (nC =1.5327) having the following analysis:

Workup

  1. temperaturewas refluxed for one hour
  2. temperatureto warm to 26° C.
  3. temperaturewas refluxed for 25 hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate concentrated in vacuo
  6. customproducing a crude product
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-edc0be9a72684bcaafa2befba400bdb0
Source dataset
uspto-grants-1982_07
Patent number
US04340416

Reaction notes

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