N,N'-Dimethylurea → 4,8-Dimethyl-6,6-bis{[methyl(methylcarbamoyl)amino]methyl}-3,9-dioxo-2,4,8,10-tetraaza-6-phosphoniaundecane 4-methylbenzene-1-sulfonate

HRID 903533Notes

Reaction equation

HRID 903533 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O-:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.O[CH2:13][P+:14]([CH2:19]O)([CH2:17]O)[CH2:15]O.[CH3:21][NH:22][C:23]([NH:25][CH3:26])=[O:24]>C1(C)C=CC=CC=1>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[CH3:21][N:22]([CH2:19][P+:14]([CH2:13][N:22]([CH3:21])[C:23]([NH:25][CH3:26])=[O:24])([CH2:15][N:22]([CH3:21])[C:23]([NH:25][CH3:26])=[O:24])[CH2:17][N:22]([CH3:21])[C:23]([NH:25][CH3:26])=[O:24])[C:23]([NH:25][CH3:26])=[O:24]

Participants

4

Reactant 2

HCID 7293N,N'-DimethylureaHCID 23463258Tetrakis(hydroxymethyl)phosphonium p-toluenesulfonate

Product 1

HCID 241994904,8-Dimethyl-6,6-bis{[methyl(methylcarbamoyl)amino]methyl}-3,9-dioxo-2,4,8,10-tetraaza-6-phosphoniaundecane 4-methylbenzene-1-sulfonateYield 89.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Reaction of tetrakis(hydroxymethyl)phosphonium p-toluenesulfonate (16.31 g, 0.05 mol) with 1,3-dimethylurea (17.62 g, 0.2 mol) in toluene (200 ml), following Example 1, gave 27.21 g (89.7%) of tetrakis(1,3-dimethylureidomethyl)phosphonium p-toluenesulfonate (I, R=R'=CH3, R"=H, X=SO3C6H4CH3 -p) as a white, crystalline solid, mp 130°-131° C. after two recrystallizations from acetonitrile. The analytical sample was dried under vacuum for 2 hr at 100° C.

Sources & evidence

ORD record
ord-27ec78882f2944eb8e10649d95e5bf45
Source dataset
uspto-grants-1980_10
Patent number
US04228100

Reaction notes

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