Triethylamine → HCID 60466690, compound

HRID 1360810Notes

Reaction equation

HRID 1360810 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][C:13]([NH2:20])([CH3:19])[CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>ClCCl>[CH3:12][C:13]([NH:20][S:8]([C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])([CH3:19])[CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61017tert-OctylamineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 60466690HCID 60466690, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Chloro-pyridine-3-sulfonyl chloride (148.0 g, 0.7 mol) was suspended in 1000 ml dry dichloromethane and added in portions over 45 minutes to a solution of 1,1,3,3-tetramethylbutylamine (465 ml 2.8 mol) and triethylamine (195 ml, 1.4 mol) in 2800 ml dry dichloromethane, keeping the temperature between −40° C. and −30° C. After addition the mixture was allowed to warm up to room temperature and stirred for an additional hour. The reaction mixture was washed three times with 1 M HCl (2000 ml each time) and twice with water (1000 ml each time). The organic layer was dried over sodium sulphate and evaporated to dryness. The residue was triturated with iso-hexane and filtered off and dried in vacuo at 40° C. to yield 90 g of the title compound.

Workup

  1. customthe temperature between −40° C. and −30° C
  2. additionAfter addition the mixture
  3. washThe reaction mixture was washed three times with 1 M HCl (2000 ml each time)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated to dryness
  6. customThe residue was triturated with iso-hexane
  7. filtrationfiltered off
  8. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-24bdb8b763484d1e8cf9bdb0878c1469
Source dataset
uspto-grants-2011_02
Patent number
US07879884B2

Reaction notes

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