Diethylamine → HCID 70548310, compound

HRID 67103Notes

Reaction equation

HRID 67103 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].Cl[CH2:7][C:8]([NH:10][C:11]1[S:12][C:13]2[C:14](=[C:16]([CH3:28])[C:17]3[N:18]=[C:19]([NH:23][C:24](=[O:27])[CH2:25]Cl)[S:20][C:21]=3[CH:22]=2)[N:15]=1)=[O:9]>O1CCOCC1>[CH2:1]([N:3]([N:23]([C:24](=[O:27])[CH3:25])[C:19]1[S:20][C:21]2[C:17](=[C:16]([CH3:28])[C:14]3[N:15]=[C:11]([N:10]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:8](=[O:9])[CH3:7])[S:12][C:13]=3[CH:22]=2)[N:18]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 151800542,6-Bis-(chloroacetyl-amino)-4-methyl-benzo[1,2-d:5,4-d']bisthiazole

Product 1

HCID 70548310HCID 70548310, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

20 gm of diethylamine were added to 11.5 gm of 2,6-bis-(chloroacetyl-amino)-4-methyl-benzo[1,2-d:5,4-d']bisthiazole in 80 ml of dioxane and the mixture was boiled for 3 hours. Then it was evaporated to dryness in vacuo, and the residue (12 gm) was chromatographed on a dry 300 gm-silicagel column with benzene/chloroform (1:1) as the mobile phase. The title compound was obtained first; 9.0 gm (66% of theory), melting point 191°-192° C., were obtained after recrystallization from alcohol.

Workup

  1. customThen it was evaporated to dryness in vacuo
  2. customthe residue (12 gm) was chromatographed on a dry 300 gm-silicagel column with benzene/chloroform (1:1) as the mobile phase

Sources & evidence

ORD record
ord-c6938d52b14d4265857b14df69f4192b
Source dataset
uspto-grants-1982_08
Patent number
US04344946

Reaction notes

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