Propyl p-toluenesulfonate → (6R)-4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine p-TSA

HRID 1897738Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]2[CH2:10][C@H:9]([NH2:11])[CH2:8][CH2:7][C:5]=2[N:6]=1.[S:12]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)([O:15][CH2:16][CH2:17][CH3:18])(=[O:14])=[O:13]>CN(C)C=O>[CH2:16]([NH:11][C@@H:9]1[CH2:8][CH2:7][C:5]2[N:6]=[C:2]([NH2:1])[S:3][C:4]=2[CH2:10]1)[CH2:17][CH3:18].[CH3:23][C:22]1[CH:24]=[CH:25][C:19]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A 1000 ml, three necked flask was equipped with an overhead stirrer, a temperature probe, a heating mantle, a claisen joint, a condenser, and a 250 ml addition funnel. The flask was charged with 25 grams of (6R)-2,6 diamino-4,5,6,7-tetrahydro-benzothiazole, followed by 200 ml of dimethyl formamide (DMF). Under continuous stirring, the mixture was heated to a temperature of 75° C. The addition funnel was charged with a solution of 39.5 grams propyl tosylate and 32.5 ml diisopropylethyleamine in 50 ml DMF. This solution was added to the 1000 ml flask dropwise over a period of 1.0 hours. The reaction was monitored by analysis on HPLC.

Workup

customA 1000 ml, three necked flask was equipped with an overhead stirrer
additiona temperature probe, a heating mantle, a claisen joint, a condenser, and a 250 ml addition funnel
additionThis solution was added to the 1000 ml flask dropwise over a period of 1.0 hours

Sources & evidence

ORD record: ord-15870e9c17454d66a336251401848db2
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519148B2

Reaction notes

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