Water → 2-Phenyl-6,7-dihydro-[1,3,4]thiadiazolo[3,2-alpha][1,3]diazepin-8(5H)-one

HRID 400369Notes

Reaction equation

HRID 400369 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][N:12]=1)=[O:6].N1CCCCC1.O>C1(C)C=CC=CC=1>[C:13]1([C:10]2[S:9][C:8]3=[N:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][N:12]3[N:11]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 84140754-chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)butanamide

Product 1

HCID 665532092-Phenyl-6,7-dihydro-[1,3,4]thiadiazolo[3,2-alpha][1,3]diazepin-8(5H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)butanamide (1.1 g, 0.004 mol) and piperidine (0.7 g, 0.8 ml, 0.008 mol) in toluene (50 ml) was heated under reflux for 3 h. The reaction mixture was cooled, poured into water and stirred. Toluene was separated dried and evaporated to give a crude product which was purified by repeated silica gel and neutral alumina column chromatography eluting with EtOAc/hexane (50:50 v/v) and CHCl3/hexane (80:20 v/v); mp 189-92° C., m/e 245, 90% (consistent with molecular formula C12H11N3OS, calcd. 245.06) 1H NMR CDCl3): δ 2.33-2.36 (m, 2H, —CH2), 2.75 (t, J=7.5 Hz, 2H, —CH2), 4.28-4.31 (t, J=7.5 Hz, 2H, —CH2), 7.46-7.52 (m, 3H, ArH), 7.94-8.10 (m, 2H, ArH). 13C NMR: δ 18.3, 31.3, 47.9, 127.4, 129.1, 130.5, 130.6, 157.4, 163.9, 173.6.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. temperatureThe reaction mixture was cooled
  4. customToluene was separated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-c745f8779e4540d8ade458dc5158828c
Source dataset
uspto-grants-2014_06
Patent number
US08741893B2

Reaction notes

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