3-Chloropropanesulphonyl chloride → HCID 10740750, compound

HRID 324982Notes

Reaction equation

[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([CH3:15])=[N:9][C:8]=2[N:7]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4].[Cl:21][CH2:22][CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26].[K+].[Br-]>>[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[N:11]([S:25]([CH2:24][CH2:23][CH2:22][Cl:21])(=[O:27])=[O:26])[C:10]([CH3:15])=[N:9][C:8]=2[N:7]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 3

HCID 154103-Chloropropanesulphonyl chloride

HCID 253877Potassium Bromide

HCID 22001644HCID 22001644, compound

Product 1

HCID 10740750HCID 10740750, compoundYield 71%

Procedure

The title compound was prepared according to the procedure of example 3 except that 1,3-dibutyl-8-methyl-3,7-dihydro-purine-2,6-dione was used in place of 1,3-dibutyl-3,7-dihydro-purine-2,6-dione and 3-chloropropanesulfonyl chloride was used in place of methanesulfonyl chloride. Yield: 71%: mp: 76-78° C.; 1H NMR (300 MHz, CDCl3): δ 0.92-0.99 (m, 6H), 1.33-1.42 (m, 4H), 1.57-1.65 (m, 2H), 1.67-1.74 (m, 2H), 2.32-2.41 (m, 2H) 2.74 (s, 3H), 3.69 (t, J=6.2 Hz, 2H), 3.99 (t, J=7.6 Hz, 2H), 4.08 (t, J=7.5 Hz, 2H), 4.23 (t, J=7.5 Hz, 2H); IR (KBr, cm−1): 2959m, 2874m, 1705s, 1620w, 1537m, 1522s, 1485m, 1183s, 1121s, 938m, 751m, 570m; MS (ES) m/z (relative intensity): 419 (M++H, 100).

Sources & evidence

ORD record: ord-97f80a42e2f6421abe489470199cc29c
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06221874B1

Reaction notes

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