N,N-Dimethyl-1,3-propanediamine → HCID 101883949, compound

HRID 2386097Notes

Reaction equation

HRID 2386097 reaction equation
[C:1]([O:11][C:12]([C:15]([CH2:18][CH2:19][S:20](Cl)(=[O:22])=[O:21])([F:17])[F:16])([F:14])[F:13])([C:4]([C:7]([F:10])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[CH3:24][N:25]([CH2:27][CH2:28][CH2:29][NH2:30])[CH3:26]>>[C:1]([O:11][C:12]([C:15]([CH2:18][CH2:19][S:20]([NH:30][CH2:29][CH2:28][CH2:27][N:25]([CH3:26])[CH3:24])(=[O:22])=[O:21])([F:17])[F:16])([F:14])[F:13])([C:4]([C:7]([F:10])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]

Participants

3

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 101883946HCID 101883946, compound

Product 1

HCID 101883949HCID 101883949, compoundYield 87.2%

Conditions

Temperature
75 °C

Procedure

C3F7OCF2CF2CH2CH2SO2Cl (100 g, 0.242 mol, 66.8% in toluene) was added dropwise to a mixture of dimethylaminopropylamine (DMAPA) at 45° C. After the addition, the reaction was heated at 75° C. overnight. The reaction mass was filtered and the wet cake was washed with 60° C. toluene. After stripping off the toluene, the concentrated organic product was washed with 200 mL of 95° C. deionized water. The product Intermediate 1, C3F7OCF2CF2CH2CH2SO2N(H)—CH2CH2CH2N(CH3)2 (101 g, 87.2%) was obtained as an amber colored solids after removing water under reduced pressure.

Workup

  1. additionAfter the addition
  2. filtrationThe reaction mass was filtered
  3. washthe wet cake was washed with 60° C. toluene
  4. washthe concentrated organic product was washed with 200 mL of 95° C.

Sources & evidence

ORD record
ord-a4aa382d5c704538ac28e4ad28562304
Source dataset
uspto-grants-2012_09
Patent number
US08268186B2

Reaction notes

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