Water → 2,6-Bis-(diethylaminoacetylamino)-benzo[1,2-d:5,4-d']bisthiazole

HRID 67102

Reaction equation

HRID 67102 reaction equation
C(N=C=NC[CH2:7][CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])C.[NH2:14][C:15]1[S:16][C:17]2[C:18](=[CH:20][C:21]3[N:22]=[C:23]([NH2:27])[S:24][C:25]=3[CH:26]=2)[N:19]=1.[CH2:28]([N:30]([CH2:35][CH3:36])[CH2:31][C:32](O)=[O:33])[CH3:29].[OH2:37]>C(Cl)Cl>[CH2:28]([N:30]([CH2:31][C:32]([NH:27][C:23]1[S:24][C:25]2[C:21](=[CH:20][C:18]3[N:19]=[C:15]([NH:14][C:7](=[O:37])[CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[S:16][C:17]=3[CH:26]=2)[N:22]=1)=[O:33])[CH2:35][CH3:36])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 74151N,N-DiethylglycineHCID 844005ST076754HCID 99645131-Ethyl-3-(3-diethylaminopropyl)carbodiimide

Product 1

HCID 151799672,6-Bis-(diethylaminoacetylamino)-benzo[1,2-d:5,4-d']bisthiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 gm of ethyl-3-(3-diethylamino-propyl)-carbodiimide was added to a suspension of 555 mgm of 2,6-diamino-benzo[1,2-d:5,4-d']bisthiazole and 655 mgm of N,N-diethyl-glycine in 20 ml of methylene chloride, and the mixture was stirred overnight at room temperature. After adding water and filtering off the precipitate, the methylene chloride phase was separated, dried, concentrated and chromatographed on a dry 10 gm-silicagel column with chloroform as the mobile phase. The title compound was collected in the first fractions and converted into the dihydrochloride by treatment with ethereal hydrochloric acid.

Workup

  1. filtrationfiltering off the precipitate
  2. customthe methylene chloride phase was separated
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed on a dry 10 gm-silicagel column with chloroform as the mobile phase
  6. customThe title compound was collected in the first fractions

Sources & evidence

ORD record
ord-3ec3306dde864a7c99f123a38144561b
Source dataset
uspto-grants-1982_08
Patent number
US04344946

Linked notes

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