Diethylamine → HCID 20205657, compound

HRID 543059Notes

Reaction equation

HRID 543059 reaction equation
[S:1]([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(C2C=CC(C)=CC=2)(=O)=O)=[CH:13][CH:12]=1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:37]([NH:39][CH2:40][CH3:41])[CH3:38]>>[CH2:37]([N:39]([CH2:40][CH3:41])[C:14]1[C:15]2[C:16](=[O:26])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23](=[O:25])[C:24]=2[C:11]([S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:2])=[O:3])=[CH:12][CH:13]=1)[CH3:38]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 20205654HCID 20205654, compound

Product 1

HCID 20205657HCID 20205657, compoundYield 91%

Procedure

1-(diethylamino)-4-tosylanthraquinone was prepared by reaction of 1,4-ditosylanthraquinone with diethyl amine. The isolated and purified reaction product has the structure illustrated below (where "Ts" is ##STR11## The yield was 91% and the m.p. 140°-141° C. Mass spec m/e 449 (M+), 434 (M-CH3), 420 (M-C2H5), 294 (M-C7H7SO2), 266 (294-CO), 155 (C7H7SO2), 91 (C7H7): H-NMR (CD2Cl2)δ8.19-8.13 (m, 2H), 7.97-7.68 (m, 4H), 7.30-7.15 (m, 4H), 3.48-3.24 (q, 4H), 2.26 (s, 3H), 1.22-1.06 (t, 6H); IR (Nujol) 1172 cm-1 (symmetrical SO2 stretch), 945 cm-1, 872, 830, 820, 800, 785, 765 (S--O--C stretch); UV/VIS max (Xylenes) 506 nm (ε3650).

Workup

  1. customThe isolated
  2. custompurified
  3. customreaction product

Sources & evidence

ORD record
ord-30f03285b2dc413cb686a11b36f503fb
Source dataset
uspto-grants-1987_04
Patent number
US04661293

Reaction notes

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