Methanol → N-methoxymethyl-N-cyclohexylsulfamic acid chloride

HRID 66263Notes

Reaction equation

HRID 66263 reaction equation
N1C(C)=CC=CC=1C.Cl[CH2:10][N:11]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[S:12]([Cl:15])(=[O:14])=[O:13].C1CCCCC1.[CH3:28][OH:29]>>[CH3:28][O:29][CH2:10][N:11]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[S:12]([Cl:15])(=[O:14])=[O:13]

Participants

5

Reactant 4

HCID 887MethanolHCID 79372,6-LutidineHCID 8078CyclohexaneHCID 53773501N-chloromethyl-N-cyclohexylsulfamic acid chloride

Product 1

HCID 53900486N-methoxymethyl-N-cyclohexylsulfamic acid chlorideYield 60%

Conditions

Temperature
45 °C

Procedure

22 parts of 2,6-lutidine are added in the course of 15 minutes, at from -5 to +5° C., to a mixture of 50 parts of N-chloromethyl-N-cyclohexylsulfamic acid chloride in 110 parts of cyclohexane and 55 parts of methanol. The reaction mixture is stirred for 20 minutes at 25° C. and one hour at 45° C. After concentrating the solvent under reduced pressure and removing the hydrochloride which has precipitated, distillation gives 30 parts (60% of theory) of N-methoxymethyl-N-cyclohexylsulfamic acid chloride of boiling point 102-106° C./0.01 mbar and nD25 = 1.4857.

Workup

  1. concentrationAfter concentrating the solvent under reduced pressure
  2. customremoving the hydrochloride which
  3. customhas precipitated
  4. distillationdistillation

Sources & evidence

ORD record
ord-447e1d0e007445bfa83340723a581ad5
Source dataset
uspto-grants-1978_12
Patent number
US04131620

Reaction notes

Loading…