Acetic Acid → HCID 21997633, compound

HRID 1977122Notes

Reaction equation

HRID 1977122 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:5]=2[N:6]=1.[OH-].[K+].C(O)(=O)C.IC[C:20]#[N:21]>O.C(O)C>[NH2:6][C:5]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:4]=1[S:3][CH2:2][C:20]#[N:21]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 14797Potassium HydroxideHCID 69356IodoacetonitrileHCID 8212032-Amino-5-fluorobenzothiazole

Product 1

HCID 21997633HCID 21997633, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent3×

Conditions

Temperature
10 °C

Procedure

A suspension of 2-amino-5-fluoro-benzothiazole (3.45 g) was stirred for 7 h at 165-170 ° C. under nitrogen in a solution of potassium hydroxide (6.9 g) in water (13.5 ml). The resulting mixture was cooled on an ice bath to 10° C., supplemented with water (5 ml) and then a solution of acetic acid (3.5 ml) in water (4 ml). The mixture was diluted with 96% ethanol (20 ml) and subsequently a solution of iodoacetonitrile (3.42 g) in 96% ethanol (5 ml) was added. After stirring for 15 min the mixture was adjusted to pH ˜7 by adding acetic acid and approx. half of the solvent was removed in vacuo. The residue was diluted with water (100 ml) and extracted with ethyl acetate (50+3×25 ml). The combined extracts were dried over sodium sulfate, filtered and evaporated to give the title compound as a practically pure yellow oil. Yield 3.60 g (96%); 1H-NMR (DMSO-d6), δ (ppm): 7.32-7.43 (dd, 1H, Ar—H), 6.49-6.60 (dd, 1H, Ar—H), 6.29-6.43 (ddd, 1H, Ar—H), 5.88 (br, 2H, NH2), 3.82 (s, 2H, CH2).

Workup

  1. customwas removed in vacuo
  2. additionThe residue was diluted with water (100 ml)
  3. extractionextracted with ethyl acetate (50+3×25 ml)
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e39d2ba7cb6d4c29821ddba9d22d3924
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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