Formaldehyde → HCID 11346466, compound

HRID 382774Notes

Reaction equation

HRID 382774 reaction equation
[CH2:1]=O.[F:3][N:4]([F:19])[C:5]([N:16]([F:18])[F:17])([CH2:11][NH:12][N+:13]([O-:15])=[O:14])[CH2:6][NH:7][N+:8]([O-:10])=[O:9]>[N+]([O-])(O)=O>[F:3][N:4]([F:19])[C:5]1([N:16]([F:17])[F:18])[CH2:11][N:12]([N+:13]([O-:15])=[O:14])[CH2:1][N:7]([N+:8]([O-:10])=[O:9])[CH2:6]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 11380095HCID 11380095, compound

Product 1

HCID 11346466HCID 11346466, compound

Reagents, catalysts & solvents 1

HCID 944Nitric AcidSolvent

Procedure

Under the conditions of nitrolysis of 2,2-bis(difluoramino)-N-(nitratomethyl)-N-nitro-N,N′-bis(4-nitrobenzenesulfonyl)-1,3-propanediamine in ca. 98% nitric acid, the liberated formaldehyde equivalent becomes available for cyclization of the N-desulfonated bis(primary nitramine), 2,2-bis(difluoramino)-N,N′-dinitro-1,3-propanediamine. The cyclization occurred spontaneously at room temperature, consuming the 2,2-bis(difluoramino)-N,N′-dinitro-1,3-propanediamine intermediate and forming 5,5-bis(difluoramino)hexahydro-1,3-dinitropyrimidine (RNFX) [1H NMR (CD3CN): δ 4.85 (s, 4 H), 6.06 (s, 2 H); 1H NMR (acetone-d6): δ 5.07 (s, 4 H), 6.31 (s, 2 H); 13C NMR (CD3CN): δ 45.3 (m, J=6 Hz), 60.6 (s) (not all carbons detected due to low S/N); 19F NMR (CD3CN): δ 29.67; 19F NMR (acetone-d6): δ 29.31)].

Workup

  1. customoccurred spontaneously at room temperature
  2. customconsuming the 2,2-bis(difluoramino)-N,N′-dinitro-1,3-propanediamine intermediate

Sources & evidence

ORD record
ord-46ff14cc9ddc4a489d19d333b5b0f1b9
Source dataset
uspto-grants-2001_10
Patent number
US06310204B1

Reaction notes

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