Propylamine → HCID 13907765, compound

HRID 1252977Notes

Reaction equation

HRID 1252977 reaction equation
[S:1]([O:11][C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:27])[C:16]=2[C:15](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:14][CH:13]=1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:39]([NH2:42])[CH2:40][CH3:41]>>[CH2:39]([NH:42][C:15]1[C:16]2[C:17](=[O:27])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24](=[O:26])[C:25]=2[C:12]([O:11][S:1]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=2)(=[O:2])=[O:3])=[CH:13][CH:14]=1)[CH2:40][CH3:41]

Participants

3

Reactant 2

HCID 7852PropylamineHCID 3841169,10-Anthracenedione, 1,4-bis[[(4-methylphenyl)sulfonyl]oxy]-

Product 1

HCID 13907765HCID 13907765, compoundYield 73%

Procedure

1-(n-propylamino)-4-tosyloxyanthraquinone was prepared by reaction of 1,4-ditosyloxyanthraquinone with n-propyl amine. The isolated and purified reaction product has the structure illustrated below (where "Ts" is ##STR9## The yield was 73% and the m.p. 163°-164° C. Mass spec m/e 435 (M+), 406 (M-C2H5), 280 (M-C7H7SO2), 252 (280-CO), 155 (C7H7SO2), 91 (C7H7); 1H-NMR (CD2Cl2)δ10.01 (br s, 1H), 8.21-7.87 (m, 2H), 7.81-7.65 (m, 4H), 7.35-6.96 (m, 4H), 3.41-3.20 (m, 2H), 2.31 (s, 3H), 1.91-1.67 (m, 2H), 1.16-1.00 (t, 3H); IR (Nujol) 1368 cm-1 (asymmetrical stretch), 1170 cm-1 (symmetric stretch), 932, 898, 865, 830, 785 cm-1 (S--O--C stretch); UV/VIS max (Xylenes) 501 nm (ε6380).

Workup

  1. customThe isolated
  2. custompurified
  3. customreaction product

Sources & evidence

ORD record
ord-b74cd724746045c69f3d837f3dba4bf4
Source dataset
uspto-grants-1988_05
Patent number
US04746461

Reaction notes

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