Acetic Acid → HCID 178463253, compound

HRID 507325Notes

Reaction equation

HRID 507325 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[S:8][C:4]=2[CH:3]=1.[CH:12](=O)[CH3:13].C(O)(=O)C.[BH3-]C#N.[Na+]>C1COCC1.O>[CH2:12]([NH:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[S:8][C:4]=2[CH:3]=1)[CH3:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178418618HCID 178418618, compound

Product 1

HCID 178463253HCID 178463253, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 100 mL two-necked flask are added 6-amino-1,3-benzothiazole-2-thiol (1.92 g, 10.5 mmol) and THF (20 mL), followed by acetaldehyde (0.591 mL, 10.5 mmol), glacial acetic acid (1 mL) and water (1 mL) at 0° C. The suspension is stirred for 1.5 hrs before a solution of NaCNBH3 (0.723 g, 10.5 mmol) in THF (20 mL) is introduced slowly through a dropping funnel. The reaction mixture is stirred at room temperature for 2 hrs after the addition. The precipitates are collected by filtration, washed with water and ether, and dried under reduced pressure to give the intermediate of 6-ethylamino-benzothiazole-2-thiol as light yellow solid (1.8 g, 82%). 1H NMR (CD3OD) δ 1.21 (t, 3H), 3.08 (q, 2H), 6.68-6.72 (m, 2H), 7.04 (d, 2H); ESIMS: m/z 211.0(M+H).

Workup

  1. additionis introduced slowly through a dropping funnel
  2. additionafter the addition
  3. filtrationThe precipitates are collected by filtration
  4. washwashed with water and ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a080481b908142a1bbdfb73ec5850fd2
Source dataset
uspto-grants-2010_08
Patent number
US07786145B2

Reaction notes

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