HCID 13015161, compound → HCID 385941, compound

HRID 1106013Notes

Reaction equation

HRID 1106013 reaction equation
[F:1][C:2]([N+:20]([O-:22])=[O:21])([N+:17]([O-:19])=[O:18])[CH2:3][N:4]([CH2:8][C:9]([N+:14]([O-:16])=[O:15])([N+:11]([O-:13])=[O:12])[F:10])[C:5](Cl)=[O:6].[F:23][C:24]([N+:30]([O-:32])=[O:31])([N+:27]([O-:29])=[O:28])[CH2:25][NH2:26]>>[F:1][C:2]([N+:20]([O-:22])=[O:21])([N+:17]([O-:19])=[O:18])[CH2:3][N:4]([CH2:8][C:9]([N+:14]([O-:16])=[O:15])([N+:11]([O-:13])=[O:12])[F:10])[C:5]([NH:26][CH2:25][C:24]([N+:30]([O-:32])=[O:31])([N+:27]([O-:29])=[O:28])[F:23])=[O:6]

Participants

3

Reactant 2

HCID 13015161HCID 13015161, compound2×HCID 130151732-Fluoro-2,2-dinitroethan-1-amine

Product 1

HCID 385941HCID 385941, compound

Procedure

A previous method for the preparation of N,N-bis(2-fluoro-2,2-dinitroethyl)carbamyl chloride (I) has been reported by W. H. Gilligan and M. J. Kamlet in U.S. Pat. No. 3,850,978, which issued on Nov. 26, 1974. However, that method suffers from the serious disadvantage that the carbamyl chloride (I) can not be separated from the reaction mixture and must be used in crude form for subsequent reactions. This drawback greatly hinders the preparation of derivatives of the carbamyl chloride (I) and heretofore certain derivatives of it could be prepared only in very low yield or not at all. For example, reaction of crude N,N-bis(2-fluoro-2,2-dinitroethyl)carbamyl chloride (prepared by the procedure of Gilligan and Kamlet, supra) with 2-fluoro-2,2-dinitroethyl amine gave none of the desired N,N,N'-tris(2-fluoro-2,2-dinitroethyl)urea. Less than a 5% yield of N,N-bis(2-fluoro-2,2-dinitroethyl)-O-(2,2,2-trinitroethyl)carbamate was obtain when the crude N,N-bis(2-fluoro-2,2-dinitroethyl)carbamyl chloride was reacted with 2,2,2-trinitroethanol.

Workup

  1. customHowever, that method suffers from the serious disadvantage that the carbamyl chloride (I) can not be separated from the reaction mixture
  2. customthe preparation of derivatives of the carbamyl chloride (I) and heretofore certain derivatives of it
  3. customcould be prepared only
  4. customin very low yield

Sources & evidence

ORD record
ord-4410621f33a04672933a56a80dfe0f50
Source dataset
uspto-grants-1982_01
Patent number
US04311649

Reaction notes

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