Propylamine → HCID 20205655, compound

HRID 543058Notes

Reaction equation

HRID 543058 reaction equation
S([C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[C:14]([S:27]([C:30]2[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=2)(=[O:29])=[O:28])=[CH:13][CH:12]=1)(C1C=CC(C)=CC=1)(=O)=O.[CH2:37]([NH2:40])[CH2:38][CH3:39]>>[CH2:37]([NH:40][C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[C:14]([S:27]([C:30]2[CH:31]=[CH:32][C:33]([CH3:34])=[CH:35][CH:36]=2)(=[O:29])=[O:28])=[CH:13][CH:12]=1)[CH2:38][CH3:39]

Participants

3

Reactant 2

HCID 7852PropylamineHCID 20205654HCID 20205654, compound

Product 1

HCID 20205655HCID 20205655, compoundYield 73%

Procedure

1-(n-propylamino)-4-tosylanthraquinone was prepared by reaction of 1,4-ditosylanthraquinone with n-propyl amine. The isolated and purified reaction product has the structure illustrated below (where "Ts" is ##STR10## 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-e270d7241650424aa742b86cf26f8bea
Source dataset
uspto-grants-1987_04
Patent number
US04661293

Reaction notes

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