Potassium Hydroxide → HCID 21997650, compound

HRID 1977114Notes

Reaction equation

HRID 1977114 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:5]=2[N:6]=1.[OH-].[K+].IC[C:17]#[N:18]>O.C(O)(=O)C.C(O)C>[NH2:6][C:5]1[C:7]([F:12])=[CH:8][C:9]([F:11])=[CH:10][C:4]=1[S:3][CH2:2][C:17]#[N:18]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 69356IodoacetonitrileHCID 7374064,6-Difluoro-1,3-benzothiazol-2-amine

Product 1

HCID 21997650HCID 21997650, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A suspension of 2-amino-4,6-difluoro-benzothiazole (7.00 g) was stirred for 6 h at 160° C. under nitrogen in a solution of potassium hydroxide (12.6 g) in water (20 ml). The resulting mixture was cooled to 0-5° C. and a solution of acetic acid (8.85 ml) in water (10 ml) and subsequently ethanol (40 ml) and iodoacetonitrile (2.75 ml) were added. After 30 min the mixture was neutralized with acetic acid (2.25 ml) and filtered. The filtrate was evaporated to approx. 30 ml and diluted with water (150 ml). A yellow precipitate was filtered off and dried. The crude product was purified by flash chromatography on silica gel eluted with ethyl acetate—heptane (3:7) yielding the title compound, Rf=0.26, as orange crystals, mp 66-67° C.; 1H-NMR (DMSO-d6), δ (ppm): 7.30-7.07 (m, 2H, Ar—H), 5.33 (br, 2H, NH2), 4.05 (s, 2H, CH2).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to approx. 30 ml
  3. additiondiluted with water (150 ml)
  4. filtrationA yellow precipitate was filtered off
  5. customdried
  6. customThe crude product was purified by flash chromatography on silica gel
  7. washeluted with ethyl acetate—heptane (3:7)

Sources & evidence

ORD record
ord-a31376f6ac634c34ba7d288a6bf772f5
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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