Water → HCID 14053646, compound

HRID 1762271Notes

Reaction equation

HRID 1762271 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([N:8]2[C:16]([Cl:17])=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:9]2)[CH:7]=1.[S-:19][C:20]#[N:21].[NH4+].BrBr.O>C(O)(=O)C>[NH2:21][C:20]1[S:19][C:3]2[CH:4]=[C:5]([F:18])[C:6]([N:8]3[C:16]([Cl:17])=[C:15]4[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]4)=[N:9]3)=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15666Ammonium thiocyanateHCID 24408BromineHCID 14053648HCID 14053648, compound

Product 1

HCID 14053646HCID 14053646, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

2-(5-Amino-2-fluorophenyl)-3-chloro-4,5,6,7-tetra-hydro-2H-indazole (22.97 g) was dissolved in 95 % aqueous acetic acid (79.53 g), and ammonium thiocyanate (15.92 g) was added thereto at room temperature (ca. 20° C). To the resultant mixture, a solution of bromine (15.89 g) in acetic acid (23.77 g) was dropwise added in 105 minutes. After being allowed to stand overnight, the mixture was heated to 100° C., and hot water (173 ml) was added thereto, followed by filtration. The filtrate was cooled and neutralized with sodium carbonate. The precipitated crystals were collected by filtration and dried to give 2-(2-amino-6-fluorobenzothiazol-5-yl)-3-chloro-4,5,6,7-tetrahydro-2H-indazole (8.77 g). m.p., 212.4° C.

Workup

  1. customat room temperature
  2. custom(ca. 20° C)
  3. filtrationfollowed by filtration
  4. temperatureThe filtrate was cooled
  5. filtrationThe precipitated crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c4f65d19fa9f43e6852fcbf88fdf8683
Source dataset
uspto-grants-1989_05
Patent number
US04831149

Reaction notes

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