Sodium Chloride → HCID 12795072, compound

HRID 648001Notes

Reaction equation

HRID 648001 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][C:23]#[N:24].[Na].[Cl-].[Na+]>ClCCl.O.ClCCl.CC(C)=O>[CH3:8][S:9]([O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][C:23]#[N:24])(=[O:11])=[O:10]

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5360545SodiumHCID 12795056HCID 12795056, compound

Product 1

HCID 12795072HCID 12795072, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

Triethylamine (31 g, 0.306 moles) and methanesulfonyl chloride (32 g, 0.279 moles) are successively added to a stirred and cooled (-8°) solution of 1-(3-hydroxypropyl)pyrrol-2-acetonitrile (38.1 g., 0.232 moles) in dichloromethane (250 ml.), maintained in an atmosphere of nitrogen, at a rate such that the reaction temperature did not exceed 0°. After a further 1 hour at this temperature (t.l.c. silica gel, dichloromethane-acetone, 95:5), saturated sodium becarbonate solution (4.4 ml.), saturated sodium chloride solution (45 ml.) and water (50 ml.) is added. The mixture is stirred for 5 min., the organic phase is separated, and combined with the dichloromethane extracts (2×100 ml.) of the aqueous phase. The extract is washed successively with saturated sodium bicarbonate solution (25 ml.), saturated sodium chloride solution (50 ml.) and water (50 ml.), and then dried over sodium sulfate. The solvent was removed in vacuo and the residual oil (77 g) is purified by chromatography on silica gel to give 42.7 g of 1-(3-methansul-fonyloxypropyl)pyrrol-2-acetonitrile (Formula (XVIII) where n is 1), (76%) was contained in the fraction eluted with hexane-dichloromethane (90:10). This product has the following physical characteristics:

Workup

  1. temperaturemaintained in an atmosphere of nitrogen, at a rate such that the reaction temperature
  2. customdid not exceed 0°
  3. stirringThe mixture is stirred for 5 min.
  4. customthe organic phase is separated
  5. washThe extract is washed successively with saturated sodium bicarbonate solution (25 ml.), saturated sodium chloride solution (50 ml.) and water (50 ml.)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe residual oil (77 g) is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7a7f7a7f25ba43ac8cf7f165836c0efc
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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