4-Aminophenylacetic acid → (2-Aminobenzothiazol-6-yl)acetic acid

HRID 655211Notes

Reaction equation

HRID 655211 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[NH4+].[N:13]#[C:14][S-:15].BrBr>C(O)(=O)C>[NH2:13][C:14]1[S:15][C:7]2[CH:6]=[C:5]([CH2:8][C:9]([OH:11])=[O:10])[CH:4]=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 145334-Aminophenylacetic acidHCID 15666Ammonium thiocyanateHCID 24408Bromine

Product 1

HCID 757163(2-Aminobenzothiazol-6-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
15 °C

Procedure

(4-Amino-phenyl)-acetic acid (20 g, 132.5 mmol) and NH4SCN (20 g, 263.2 mmol) were dissolved in 300 ml of acetic acid and the mixture was cooled to 15° C., treated with Br2 (21.2 g, 6.8 ml) in acetic acid (10 ml) and the temperature did not exceed 15° C. Then the reaction was stirred at room temperature for 4 h. The mixture was filtered and the cake was re-dissolved in water, adjusted the pH=5. The precipitate was filtered and dried to obtain 2-amino-benzothiazol-6-yl)-acetic acid as light yellow powder (24 g, 87.1%).

Workup

  1. customdid not exceed 15° C
  2. filtrationThe mixture was filtered
  3. dissolutionthe cake was re-dissolved in water
  4. filtrationThe precipitate was filtered
  5. customdried
  6. customto obtain 2-amino-benzothiazol-6-yl)-acetic acid as light yellow powder (24 g, 87.1%)

Sources & evidence

ORD record
ord-cedaabdfe45a46bfbb30c10fb27171c5
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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