Water → HCID 21997544, compound

HRID 1977262Notes

Reaction equation

HRID 1977262 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:31]=[CH:30][C:13]([C:14]([NH:16][NH:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)=O)=[CH:12][CH:11]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:33].O>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:31]=[CH:30][C:13]([C:14]2[S:33][C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=3)=[N:17][N:16]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 21997580HCID 21997580, compound

Product 1

HCID 21997544HCID 21997544, compoundYield 165.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-[4-(6-methoxy-n-hexyloxy)benzoyl]-N′-(4-methoxycarbonylbenzoyl)hydrazine (193.4 g) and phosphorus pentasulfide (113.34 g) in tetrahydrofuran (2.5 L) was heated to reflux for 1 hour then cooled to room temperature and poured into water (7 L). The resulting precipitate was collected by filtration, washed thoroughly with water then partially dried. The solid was added to 1:1 CH3CN—H2O (200 ml), sitrred then filtered. This procedure was repeated a further 2 times, and the resulting yellow powder washed thoroughly with acetonitrile (500 ml×5) then dried under hi-vacuum at 50° C. to give methyl 4-[5-[4-(6-methoxy-n-hexyloxy)phenyl]-1,3,4-thiadiazol-2-yl]benzoate (179.6 g) as a yellow powder.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed thoroughly with water
  5. customthen partially dried
  6. additionThe solid was added to 1:1 CH3CN—H2O (200 ml)
  7. filtrationsitrred then filtered
  8. washthe resulting yellow powder washed thoroughly with acetonitrile (500 ml×5)
  9. customthen dried under hi-vacuum at 50° C.

Sources & evidence

ORD record
ord-9599b8bfffbf4feeba657d23dc68960b
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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