Hydrochloric Acid → HCID 53714462, compound

HRID 443096Notes

Reaction equation

HRID 443096 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[F:5][C:6]([C:41]([F:44])([F:43])[F:42])([O:10][C:11]([F:40])([F:39])[C:12]([F:38])([C:34]([F:37])([F:36])[F:35])[O:13][C:14]([F:33])([F:32])[C:15]([F:31])([C:27]([F:30])([F:29])[F:28])[O:16][C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[C:7](F)=[O:8].Cl>>[CH2:1]([NH:4][C:7](=[O:8])[C:6]([F:5])([C:41]([F:42])([F:43])[F:44])[O:10][C:11]([F:39])([F:40])[C:12]([F:38])([C:34]([F:35])([F:36])[F:37])[O:13][C:14]([F:32])([F:33])[C:15]([F:31])([C:27]([F:30])([F:29])[F:28])[O:16][C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7853AllylamineHCID 119616Perfluoro-2,5,8-trimethyl-3,6,9-trioxadodecanoyl fluoride

Product 1

HCID 53714462HCID 53714462, compoundYield 99%

Procedure

A 100 mL round bottom flask equipped with a magnetic stirring bar and an addition funnel was charged with 9.0 g of allyl amine (160 mmoles). The liquid was stirred and 40 g of 97% perfluoro-2,5,8-trimethyl-3,6,9-trioxadodecanoyl fluoride (60 mmoles) was added dropwise. Dilute hydrochloric acid was added to the flask and the two phase mixture was transferred into a separatory funnel and the aqueous layer separated from the amide layer. The amide layer was washed again with dilute hydrochloric acid and twice with water. The amide layer was transferred into a round bottom flask and distilled at 101° C. and 3 mmHg to yield a fraction of 21.6 (52% yield) of >99% N-allylperfluoro-2,5,8-trimethyl-3,6,9-trioxadodecanamide (31 mmoles).

Workup

  1. customA 100 mL round bottom flask equipped with a magnetic stirring bar and an addition funnel
  2. customthe two phase mixture was transferred into a separatory funnel
  3. customthe aqueous layer separated from the amide layer
  4. washThe amide layer was washed again with dilute hydrochloric acid and twice with water
  5. customThe amide layer was transferred into a round bottom flask
  6. distillationdistilled at 101° C.

Sources & evidence

ORD record
ord-a63bdc47a3d640eba5778a463e93869e
Source dataset
uspto-grants-1999_04
Patent number
US05892086

Reaction notes

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