Hydrogen Bromide → HCID 131715865, compound

HRID 1382538Notes

Reaction equation

HRID 1382538 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[N:8]=[C:7]3[C:20]4[CH:26]=[C:25]([O:27]C)[CH:24]=[CH:23][C:21]=4[S:22][C:5]=1[C:6]=23.B(Br)(Br)[Br:30].ClCCl.Br>ClCCCl.CO>[BrH:30].[NH2:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[N:8]=[C:7]3[C:20]4[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][C:21]=4[S:22][C:5]=1[C:6]=23

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 25134Boron tribromide2×HCID 21274743HCID 21274743, compound2×

Product 1

HCID 131715865HCID 131715865, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

A solution of 98 g (0.222 mol) of 5-amino-N,N-diethyl-9-methoxy-2H-[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine dihydrochloride (Compound 1A), in 900 ml 1,2-dichloroethane, was treated with 444 ml of a 1M solution of boron tribromide in dichloromethane (0.444 mol). The mixture was heated to 50° C. for 24 hours at which time 200 ml of the boron tribromide solution (0.200 mol) were added, and the reaction maintained at 50° for an additional 24 hours. The mixture was cooled, and methanol (600 ml) was carefully added. The mixture was heated under reflux for three hours, then cooled at 0° for 48 hours. The yellow precipitate was collected by suction filtration, washed with cold methanol, then dried at 60°, 200 mm Hg, affording 110.4 g of 5-amino-2-[2-(diethylamino)ethyl]-2H-[1]benzothiopyrano[4,3,2-cd]indazol-9-ol, hydrobromide with 1.8 equivalents of hydrogen bromide, mp 305° (decomposition), 98.36% pure by HPLC.

Workup

  1. additionwere added
  2. temperaturethe reaction maintained at 50° for an additional 24 hours
  3. temperatureThe mixture was cooled
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for three hours
  6. temperaturecooled at 0° for 48 hours
  7. filtrationThe yellow precipitate was collected by suction filtration
  8. washwashed with cold methanol
  9. customdried at 60°

Sources & evidence

ORD record
ord-6bb6d3ee3d354287976a212aee2ab926
Source dataset
uspto-grants-1989_02
Patent number
US04806654

Reaction notes

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