Dichloromethane → HCID 59324100, compound

HRID 1639712Notes

Reaction equation

HRID 1639712 reaction equation
[OH:1][CH:2]([CH2:5][O:6][CH3:7])[C:3]#[N:4].ClCCl.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>O>[C:3]([CH:2]([O:1][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:5][O:6][CH3:7])#[N:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1471518693177-83-4

Product 1

HCID 59324100HCID 59324100, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

27.3 gr (0.27 Mol) of 2-hydroxy-3-methoxy-propionitrile was dissolved dichloromethane (250 ml) and treated first with 56.4 ml (0.40 Mol) triethylamine keeping the temperature below −8° C., followed by dropwise addition of 23.1 ml (0.297 mol) methansulfonyl chloride keeping the temperature below +7° C. under cooling. After the exothermic reaction ceased the mixture was left to reach room-temperature. Water was stirred in, and the mixture was extracted with tert.-butylmethylether, washed with brine, dried and evaporated. To remove some polar side-products the crude liquid obtained was filtered through silica gel (eluent: cyclohexane/ethylacetate 1:1). Methanesulfonic acid 1-cyano-2-methoxy-ethyl ester of 89% purity (GC-MS) was obtained; 1H-NMR (CDCl3): 5.33, t, 1H, 3.81, d, 2H, 3.48, s, 3H, 3.21, s, 3H.

Workup

  1. temperatureunder cooling
  2. customAfter the exothermic reaction
  3. waitwas left
  4. extractionwas extracted with tert.-butylmethylether
  5. washwashed with brine
  6. customdried
  7. customevaporated
  8. customTo remove some polar side-products the crude liquid
  9. customobtained
  10. filtrationwas filtered through silica gel (eluent: cyclohexane/ethylacetate 1:1)

Sources & evidence

ORD record
ord-15dfb02a883f4738b88b0e9cded62a90
Source dataset
uspto-grants-2012_02
Patent number
US08110593B2

Reaction notes

Loading…