Ammonia → HCID 22989134, compound

HRID 990292Notes

Reaction equation

HRID 990292 reaction equation
C[N:2](C(N=NC(N(C)C)=O)=O)C.[C:13]([OH:22])(=[O:21])/[CH:14]=[CH:15]/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19].[NH3:23]>>[NH2:23][CH:16]([CH:15]([NH2:2])[CH2:14][C:13]([OH:22])=[O:21])[CH2:17][C:18]([OH:20])=[O:19]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 5356793Muconic Acid2×

Product 1

HCID 22989134HCID 22989134, compound

Procedure

The bicyclic dilactam of 3,4-diamino-1,6-hexanedioic acid was synthesised via the diamide of muconic acid (2,4-hexadiene-1,6-dioic acid) essentially as outlined by Köhl in Berichte 35, 173 (1903). In a modification of Köhl's procedure, the dimethylester of trans, trans-muconic acid (13.6 g=0.080 mole) was autoclaved for 5 hours at 150° C. with 60 ml 32% aqueous ammonia. The resulting solution on evaporation and cooling yielded 1.40 g of crystalline dilactam.

Workup

  1. customThe resulting solution on evaporation
  2. temperaturecooling

Sources & evidence

ORD record
ord-c4e8b623308546fea83f9e9023a034a7
Source dataset
uspto-grants-2002_10
Patent number
US06458980B1

Reaction notes

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