Ammonia → HCID 11472050, compound

HRID 1370706Notes

Reaction equation

[S-:1][C:2]#[N:3].[K+].[CH:5]1[C:17]2[CH:16]([CH2:18][O:19][C:20](Cl)=[O:21])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.[NH3:23].C(O)C>C(OCC)(=O)C>[C:20]([NH:3][C:2]([NH2:23])=[S:1])([O:19][CH2:18][CH:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2[C:17]1=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of potassium thiocyanate (8.55 g, 88 mmol) in ethyl acetate (100 mL) cooled to 0° C. was added dropwise a solution of 9-fluorenylmethoxycarbonyl chloride (20.7 g, 80 mmol) in ethyl acetate (100 mL) over a period of 15 min. The resulting suspension was allowed to warm to ambient temperature overnight with stirring. The formed solid was filtered off and the filtrate was concentrated in vacuo to afford an orange oil. Without further purification, the oil was dissolved in ethanol (50 mL) and treated by dropwise addition with a cold solution of ammonia in ethanol (7N, 91 mL, 637 mmol). A precipitate formed upon addition of the ammonia solution. The suspension was stirred vigorously at 0° C. for 15 min and then the solids were filtered off, washed with cold ethanol (3×20 mL) and dried to afford N-Fmoc-thiourea (16.8 g, 70%) as an off-white solid: EI-HRMS m/e calcd for C16H14N2O2S (M+) 298.0776, found 298.0770.

Workup

temperatureto warm to ambient temperature overnight
filtrationThe formed solid was filtered off
concentrationthe filtrate was concentrated in vacuo
customto afford an orange oil
customWithout further purification
dissolutionthe oil was dissolved in ethanol (50 mL)

Sources & evidence

ORD record: ord-4769b793109a49019ffa3f19aa481f9f
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583288B2

Reaction notes

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