Butylamine → N-Butyl-N'-{2-[(E)-tert-butyldiazenyl]-4-methylpentan-2-yl}thiourea

HRID 436761Notes

Reaction equation

[C:1]([N:5]=[N:6][C:7]([N:13]=[C:14]=[S:15])([CH2:9][CH:10]([CH3:12])[CH3:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([NH2:20])[CH2:17][CH2:18][CH3:19]>CCCCC>[C:1]([N:5]=[N:6][C:7]([NH:13][C:14]([NH:20][CH2:16][CH2:17][CH2:18][CH3:19])=[S:15])([CH3:8])[CH2:9][CH:10]([CH3:11])[CH3:12])([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: 30 °C

Procedure

To 22.65 grams (0.1 mole) of 2-t-butylazo-2-isothiocyanato-4-methylpentane stirred with a magnetic stirrer in a 125 ml erlenmeyer flask was slowly added 7.7 grams (0.105 mole) of n-butylamine. After the addition was complete, the reaction mixture was stirred for 3 hours at 30° C., dissolved in pentane, transferred to a round bottom flask and the pentane evaporated under reduced pressure. The residue was then stripped under high vacuum to remove any low boilers. The residue weighed 30 grams (100% yield) and its infrared spectrum contained peaks around 1500-1550 cm-1 which appears to be due to the ##STR56## group and NH peaks around 3350 cm-1. The isothiocyano band around 2040 cm-1 had disappeared.

Workup

additionAfter the addition
customtransferred to a round bottom flask
customthe pentane evaporated under reduced pressure
customto remove any low boilers

Sources & evidence

ORD record: ord-cfc91ae60b9345d9a50d7643eafd97ac
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04028344

Reaction notes

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