Potassium Hydroxide → HCID 66707209, compound

HRID 911724Notes

Reaction equation

HRID 911724 reaction equation
O[CH2:2][C:3]1[S:4][CH:5]=[N:6][N:7]=1.[C:8]([O:12][C:13]([N:15]1[CH2:21][CH2:20][C:19]2[C:22]([S:26]C(=O)N(C)C)=[CH:23][CH:24]=[CH:25][C:18]=2[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[OH-].[K+].S(Cl)([Cl:36])=O>CO>[C:8]([O:12][C:13]([N:15]1[CH2:21][CH2:20][C:19]2[C:22]([S:26][CH2:2][C:3]3[S:4][CH:5]=[N:6][N:7]=3)=[C:23]([Cl:36])[CH:24]=[CH:25][C:18]=2[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 24386Thionyl ChlorideHCID 21320043(1,3,4-Thiadiazol-2-yl)methanolHCID 86629693HCID 86629693, compound

Product 1

HCID 66707209HCID 66707209, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir 2-hydroxymethyl-[1,3,4]-thiadiazole (241 mg, 2.1 mmol) in thionylchloride (5 mL) for 1 h and concentrate in vacuo. Treat this residue with the thiolate prepared from 3-tert-butoxycarbonyl-6-dimethylcarbamoylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.4 g, 1.04 mmol) and potassium hydroxide (1.37 g, 24.5 mmol) in methanol (3.5 mL) according to General Procedure 7 to give 3-tert-butoxycarbonyl-7-chloro-6-([1,3,4]thiadiazol-2-yl-methylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.3 g, 70%). Treat an aliquot with trifluoroacetic acid to obtain the mass spectrum. MS (ES+) m/z: 312 (M+H)+.

Workup

  1. concentrationconcentrate in vacuo
  2. additionTreat this residue with the thiolate

Sources & evidence

ORD record
ord-37b6a972687c41748735757f9c398803
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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