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Ammonia → Malonyldiamide, N,N'-bis(trimethylsilyl)-

HRID 435192
Notes
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Reaction equation

HRID 435192 reaction equation
C[Si](C)(C)[NH:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[C:10]([NH2:16])(=[O:15])[CH2:11][C:12](N)=[O:13].S(=O)(=O)(O)O.N>S1(C2C(=CC=CC=2)C(=O)N1)(=O)=O.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:5][Si:4]([CH3:7])([CH3:6])[NH:16][C:10](=[O:15])[CH2:11][C:12]([NH:3][Si:4]([CH3:5])([CH3:6])[CH3:7])=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 7911MalonamideHCID 13838Hexamethyldisilazane

Product 1

HCID 554458Malonyldiamide, N,N'-bis(trimethylsilyl)-Yield 99,004.203%

Reagents, catalysts & solvents 3

HCID 5143Saccharin
Catalyst
HCID 1049PyridineSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

7.5 ml (36 mmoles) of hexamethyldisilazane were added to a refluxing mixture of 3.06 g (0.03 mmole) of malonamide, 18.3 mg (0.1 mmole) of saccharin, 50 ml of ethyl acetate and 5 ml of pyridine and by titrating with 1 N sulfuric acid the ammonia evolved, it was found that 30 mmoles were expelled after refluxing for one hour. Volatile material was vacuum evaporated and the residue, which crystallized upon standing, was dried in vacuo to obtain 7.32 g (99%) of N,N'-bis-(trimethylsilyl)-malonamide melting at 72°-76° C. NMR Spectrum (CDCl3): Δ0.24 (s, 18H); 3.20 (s, 2H); 6.5 (broad, 2H).

Workup

  1. temperatureafter refluxing for one hour
  2. customevaporated
  3. customthe residue, which crystallized
  4. customwas dried in vacuo

Sources & evidence

ORD record
ord-26864b483c4f4499ba9816be3ef8ef45
Source dataset
uspto-grants-1983_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04400509

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes