2-Mercaptoethanol → 2-[(3,6-Dichloro-4-pyridazinyl)thio]ethanol

HRID 15152

Reaction equation

HRID 15152 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1Cl.[SH:10][CH2:11][CH2:12][OH:13].C(=O)(O)[O-].[Na+].ClCCl>O1CCCC1.C(N(CC)CC)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[S:10][CH2:11][CH2:12][OH:13]

Participants

7

Reactant 4

HCID 15672-MercaptoethanolHCID 6344DichloromethaneHCID 951233,4,6-TrichloropyridazineHCID 516892Sodium Bicarbonate

Product 1

HCID 817660832-[(3,6-Dichloro-4-pyridazinyl)thio]ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3,4,6-trichioropyridazine (25 g) in tetrahydrofuran (200 ml) and triethylamine (19 ml) was treated at 0° C. (ice bath cooling) with 2-mercaptoethanol (8.33 ml) over 5 minutes. After the addition was complete, the mixture was stirred at room temperature for 72 hours. The mixture was stirred with aqueous sodium bicarbonate solution and dichloromethane and the solid was collected, washed with water, ether and pentane and dried in vacuo, giving (22.9 g). The combined aqueous and organic fraction was evaporated to half volume giving further solid, which was washed and dried as above (5.0 g). The total yield of solid (27.9 g; 91%) contained some bromo-analogue (5-10%) by NMR.

Workup

  1. additionAfter the addition
  2. customthe solid was collected
  3. washwashed with water, ether and pentane
  4. customdried in vacuo
  5. customgiving (22.9 g)
  6. customThe combined aqueous and organic fraction was evaporated to half volume
  7. customgiving further solid, which
  8. washwas washed
  9. customdried as above (5.0 g)

Sources & evidence

ORD record
ord-ac95521bbf7746a397c2d885666fc1aa
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Linked notes

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