Toluene → Ethyl 2-[6-fluoro-3-(2-propenyl)-2(3H)-benzothiazolon-5-ylaminothiocarbonyl]hexahydropyridazine-1-carboxylate

HRID 1199145Notes

Reaction equation

HRID 1199145 reaction equation
[F:1][C:2]1[C:14]([N:15]=[C:16]=[S:17])=[CH:13][C:5]2[N:6]([CH2:10][CH:11]=[CH2:12])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.[N:18]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][NH:19]1.C1(C)C=CC=CC=1.C(N(CC)CC)C>O>[F:1][C:2]1[C:14]([NH:15][C:16]([N:19]2[CH2:20][CH2:21][CH2:22][CH2:23][N:18]2[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[S:17])=[CH:13][C:5]2[N:6]([CH2:10][CH:11]=[CH2:12])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 30143771(2H)-Pyridazinecarboxylic acid, tetrahydro-, ethyl esterHCID 143064856-Fluoro-3-(2propenyl)-2(3H)-benzothiazolon-5-yl isothiocyanate

Product 1

HCID 14306486Ethyl 2-[6-fluoro-3-(2-propenyl)-2(3H)-benzothiazolon-5-ylaminothiocarbonyl]hexahydropyridazine-1-carboxylateYield 105.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Fluoro-3-(2-propenyl)-2(3H)-benzothiazolon-5-yl isothiocyanate (3.1 g) and ethyl hexahydropyridazine-1-carboxylate (1.17 g) were added to toluene (15 ml). A catalytic amount of triethylamine was added thereto, and the resultant mixture was stirred at 25° C. for 12 hours. Water was added thereto, and the resultant mixture was extracted with toluene. The extract was washed with water, dried and concentrated to give ethyl 2-[6-fluoro-3-(2-propenyl)-2(3H)-benzothiazolon-5-ylaminothiocarbonyl]-hexahydropyridazine-1-carboxylate (3.3 g). m.p., 40°-42° C.

Workup

  1. extractionthe resultant mixture was extracted with toluene
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b763ad7619374862941e0d9490916fef
Source dataset
uspto-grants-1990_02
Patent number
US04898948

Reaction notes

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