Tetrahydrofuran → HCID 19598372, compound

HRID 1957402Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])=[CH:20][CH:19]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[C:36]1(C(Cl)=O)[C:49]2[C:40](=[N:41][C:42]3[C:47]([CH:48]=2)=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:39]=[CH:38][CH:37]=1.CN(C1C=CC=CN=1)C.[O:62]1CCC[CH2:63]1>>[CH2:8]([O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N:24]([S:25]([C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)(=[O:27])=[O:26])[C:63]([C:48]2[C:47]3[C:42]([N:41]=[C:40]4[C:49]=2[CH:36]=[CH:37][CH:38]=[CH:39]4)=[CH:43][CH:44]=[CH:45][CH:46]=3)=[O:62])=[CH:20][CH:19]=1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Reactant 5

HCID 8028Tetrahydrofuran2×

HCID 8471Triethylamine

HCID 218852-Dimethylaminopyridine

HCID 18704208HCID 18704208, compound

HCID 19598386HCID 19598386, compound

Product 1

HCID 19598372HCID 19598372, compound

Conditions

Temperature: 600 °C

Procedure

2.1 ml (15 mmol) of triethylamine in 10 ml of tetrahydrofuran are added dropwise at 25° C. to a solution of 1.5 g (4 mmol) of N-(4-benzyloxycarbonylphenyl)-4-toluenesulfonamide, 1.23 g (4.4 mmol) of acridinecarbonyl chloride hydrochloride and 0.02 g of dimethylaminopyridine in 20 ml of anhydrous tetrahydrofuran. The temperature is raised to 600° C.

Sources & evidence

ORD record: ord-7f9d6b98b44147b0ae593d7420a551e8
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783696

Reaction notes

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