HCID 178460303, compound → HCID 178512720, compound

HRID 612840Notes

Reaction equation

HRID 612840 reaction equation
C([O-])(C)C.[NH2:5][C:6](=[N:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][S:15][CH2:16][CH2:17][NH:18][CH:19]=[N:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[N:13]=1)[NH2:7]>CO>[CH:25]1[C:24]([S:21](/[N:20]=[CH:19]/[NH:18][CH2:17][CH2:16][S:15][CH2:14][C:12]2[N:13]=[C:9]([NH:8][C:6]([NH2:7])=[NH:5])[S:10][CH:11]=2)(=[O:22])=[O:23])=[CH:29][CH:28]=[C:27]([Br:30])[CH:26]=1

Participants

3

Reactant 1

HCID 178460303HCID 178460303, compound

Product 1

HCID 178512720HCID 178512720, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

57.9 g of N-[[[2-[[[2-[(diaminomethylene)amino]-4-thiazolyl]methyl]thio]ethyl]amino]methylene]-4-bromo-benzenesulfonamide isopropanolate are dissolved in 87 ml of methanol at a temperature ranging between 40 and 50° C. The resultant solution is allowed to stand till a certain degree of turbidness fades away, then filtered and poured onto 550 ml of water at 0-5° C. for 4 hours under energic stirring. After the addition is completed, the mixture is stirred for further 4 hours at 0-5° C. and filtered. The filtrate is washed with abundant water and dried in vacuo at a temperature below 30° C. to yield 49.9 g of ebrotidine Form A.

Workup

  1. customranging between 40 and 50° C
  2. filtrationfiltered
  3. additionpoured onto 550 ml of water at 0-5° C. for 4 hours under energic stirring
  4. additionAfter the addition
  5. filtrationfiltered
  6. washThe filtrate is washed with abundant water
  7. customdried in vacuo at a temperature below 30° C.

Sources & evidence

ORD record
ord-760600ac62424a51b154b28f5b829542
Source dataset
uspto-grants-1999_12
Patent number
US06005115

Reaction notes

Loading…