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N,N'-Dimethylurea → Tetrakis(1,3-dimethylureidomethyl)phosphonium iodide

HRID 903531
Notes
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Reaction equation

HRID 903531 reaction equation
[I-:1].O[CH2:3][P+:4]([CH2:9]O)([CH2:7]O)[CH2:5]O.[CH3:11][NH:12][C:13]([NH:15][CH3:16])=[O:14]>C1(C)C=CC=CC=1>[I-:1].[CH3:11][N:12]([CH2:9][P+:4]([CH2:3][N:12]([CH3:11])[C:13]([NH:15][CH3:16])=[O:14])([CH2:5][N:12]([CH3:11])[C:13]([NH:15][CH3:16])=[O:14])[CH2:7][N:12]([CH3:11])[C:13]([NH:15][CH3:16])=[O:14])[C:13]([NH:15][CH3:16])=[O:14]
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7293N,N'-DimethylureaHCID 3017915Tetrakis(hydroxymethyl)phosphanium iodide

Product 1

HCID 24199281Tetrakis(1,3-dimethylureidomethyl)phosphonium iodideYield 97.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Reaction of tetrakis(hydroxymethyl)phosphonium iodide (7.05 g, 0.025 mol) with 1,3-dimethylurea (8.81 g, 0.1 mol) in toluene (25 ml), following Example 1, gave 13.65 g (97.1%) of tetrakis(1,3-dimethylureidomethyl)phosphonium iodide (I, R=R'=CH3, R"=H, X=I) as a white, crystalline solid, mp 194° C. dec after two recrystallizations from ethanol (10 ml/g). The product suffered no weight loss when dried under vacuum for 2 hr at 100° C.

Sources & evidence

ORD record
ord-d1f8272b09834e28a0c7fc442d887825
Source dataset
uspto-grants-1980_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04228100

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes