Methanol → HCID 131716048, compound

HRID 1085691Notes

Reaction equation

HRID 1085691 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][CH:7]1[CH2:9][O:8]1.Br.[CH3:14][N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[S:17][C:16]1=[N:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[C:31](=[O:34])([O-:33])[O-].[Na+].[Na+].C[OH:38]>CC1C=CC=CC=1>[C:9]([OH:8])(=[O:38])/[CH:7]=[CH:6]\[C:31]([OH:33])=[O:34].[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][CH:7]([OH:8])[CH2:9][N:28]1[CH2:29][CH2:30][CH:25]([N:24]=[C:16]2[N:15]([CH3:14])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[S:17]2)[CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 98990282211-95-2HCID 20060610HCID 20060610, compound

Product 1

HCID 131716048HCID 131716048, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.77 parts of [(3-chlorophenoxy)methyl]oxirane, 4.92 parts of N-(3-methyl-2(3H)-benzothiazolylidene)-4-piperidinamine monohydrobromide, 2.12 parts of sodium carbonate, 60 parts of methanol and 68 parts of methylbenzene was stirred and refluxed overnight. The reaction mixture was cooled and the solvent was evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol (99:1 by volume), as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (Z)-2-butenedioate salt in 2-propanol and methanol. The salt was filtered off and dried, yielding 5.5 parts (55%) of α-[(3-chlorophenoxy)methyl]-4-[(3-methyl-2(3H)-benzothiazolyliden)amino]-1-piperidineethanol (Z)-2-butenedioate(1:2); mp. 157.6° C. (428).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was evaporated
  4. filtrationThe residue was purified by filtration over silica gel using
  5. additiona mixture of trichloromethane and methanol (99:1 by volume)
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. filtrationThe salt was filtered off
  9. customdried

Sources & evidence

ORD record
ord-6183dda8e76245c483c2eb000841be75
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Reaction notes

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