Dimethylformamide → HCID 86744558, compound

HRID 704719Notes

Reaction equation

HRID 704719 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:12]1.Cl.Cl[CH2:25][C:26]1[N:27]=[CH:28][S:29][CH:30]=1.[C:31](=[O:34])([O-:33])[O-].[Na+].[Na+].CN(C)[CH:39]=[O:40]>O>[C:39]([OH:40])(=[O:19])/[CH:26]=[CH:30]/[C:31]([OH:33])=[O:34].[S:29]1[CH:30]=[C:26]([CH2:25][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[NH:10][CH:11]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:12]2)[N:27]=[CH:28]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium Carbonate2×HCID 27632894-(Chloromethyl)-1,3-thiazole hydrochloride2×HCID 15037356HCID 15037356, compound

Product 1

HCID 86744558HCID 86744558, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6 parts of ethyl 4-(1H-benzimidazol-2-ylamino)hexahydro-1H-azepine-1-carboxylate, 3.75 parts of 4-(chloromethyl)thiazole hydrochloride, 5.3 parts of sodium carbonate and 90 parts of N,N-dimethylformamide was stirred overnight at 70° C. Another amount of 4-(chloromethyl)thiazole hydrochloride and sodium carbonate were added and stirring was continued overnight at 70° C. After cooling, the reaction mixture was poured into water. The product was extracted with methylbenzene. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (E)-2-butenedioate salt in ethanol. The salt was filtered off and dried, yielding 1.4 parts (13.5%) of ethyl hexahydro-4-[[1-(4-thiazolylmethyl)-1H-benzimidazol-2-yl]amino]-1H-azepine-1-carboxylate (E)-2-butenedioate (1:1); mp. 143.7° C. (compound 27).

Workup

  1. stirringstirring
  2. waitwas continued overnight at 70° C
  3. temperatureAfter cooling
  4. extractionThe product was extracted with methylbenzene
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationThe salt was filtered off
  13. customdried

Sources & evidence

ORD record
ord-dfc02fad763f405ea3eecb2c7161e8e8
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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